Fragmentation Route of doubly ionized benzene, aniline, and nitroanilines monomers using a novel protocol from density functional theory and QTAIM

Fragmentation Route of doubly ionized benzene, aniline, and nitroanilines monomers using a novel protocol from density functional theory and QTAIM | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Fragmentation Route of doubly ionized benzene, aniline, and nitroanilines monomers using a novel protocol from density functional theory and QTAIM Carlos X. Oliveira, Fabio L.P. Costa, Gunar V. S. Mota This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-1825286/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 26 Jan, 2023 Read the published version in Journal of Molecular Modeling → Version 1 posted 7 You are reading this latest preprint version Abstract The possibility of finding the fragmentation routes by theoretical methods, led us to compare the molecular ions between neutral molecules of benzene, aniline, and o -, m -, and p -nitroaniline, using the Density Functional Theory (DFT), under an aug-cc-pVDZ base set and a B3LYP exchange-correlation functional. After determining the structure and electronic energy of neutral and doubly ionized species, we used a new protocol based on the analysis of Wiberg's binding indexes and the quantum theory of atoms in Bader molecules (QTAIM). Where the charge transfer and electronic distribution in aromatic monomers indicate the possibility of fragment formation in at least two pairs of carbon-carbon (CC) atoms and indicate the possible loss of the -CNH 2 and -NO 2 groups in the aniline and nitroaniline molecules doubly ionized. Aromatic monomers Fragmentation pathway QTAIM analysis Wiberg’s bond order indices Figures Figure 1 Figure 2 Figure 3 Figure 4 1. Introduction The studies of mass spectrometry are focused on the analysis of the fragmentation of species present in the ionosphere of extraterrestrial planets that, in their states of charge 2+ (doubly charged), which suggests a possible way of molecular fragmentation, formed by pairs of atoms in molecules of the same chemical species, but in different charge states [ 1 ]. Molecules, such as benzene, which in its gaseous phase have an aromatic ring with amine, and nitro groups in your structure, are known as push-pull molecules, characterized by groups of donors and acceptors of electrons between pi -conjugated bonds [ 2 ],[ 3 ]. In recent studies of time-of-flight mass spectrometry (TOF), double-ionized benzene monomer was observed in dissociative processes, when excited by synchrotron radiation [ 4 ]. These stable nitroaromatic fragments have significant concentrations of charges (or electron densities), which can form a metastable state [ 5 – 8 ]. The systems formed by benzene clusters, doubly ionized, are based on the cationic benzene dimer [C6H6] 2+ , and the dicationic benzene monomer in the C6H6 2+ . They exhibit structural patterns from a variety of low-energy conformations of the cation benzene dimer and dicationic benzene [ 5 ]. The nitroanilines are the simpler examples of molecules with highly polar regions, which are constituted by the aromatic fragment of the electrons group's donors, and acceptors. The absorption spectra of the electronic transitions of aromatic molecules (nitroanilines) were studied. Moreover, the aromatic molecules that have electron acceptor groups -NO 2 , show a stronger absorption, associated with the intramolecular charge transfer, in the region of ultraviolet [ 6 ],[ 7 ]. The theoretical results provide a reasonable framework for the interpretation of the complex structure of the spectrum of para -nitroaniline and the major differences in the spectrum of meta -nitroaniline [ 8 ]. The new techniques of elucidation of the formation of molecular fragments for different chemical species lead to the emergence of different forms of theoretical methodology to study the fragmentation of benzene, aniline, and ortho -, meta - and para -nitroaniline [ 13 – 20 ]. To connect the theory to the experiment, we calculated the electronic structure of the molecules, using a new protocol[ 9 ] applied to benzene (BZ), aniline (ANI), and the nitroanilines (NA) in conformations ortho -, meta - and para - (named oNA, mNA, and pNA, respectively) for the neutral and doubly ionized molecules to understand the dynamics of fragmentation of these molecules. But, to achieve this, we evaluate the bond order by Wiberg's bond index to identify the probable places of bonds break [ 10 ], and also we had made an analysis of the density of electronics on the bonds by Quantum Theory of Atoms In Molecules (QTAIM) to distinguish the different concentrations of charge in pairs of atoms [ 11 ]. 2. Methodology All our calculations of first principles were performed using the Gaussian software (release 09)[ 12 ] applied to the molecular structure of the benzene, aniline, o-, m-, and p-nitroaniline, at different levels (neutrals, and ions), the existing basic formalism of Density Functional Theory (DFT) method [ 13 ][ 14 ], with a B3LYP hybrid functional introduced by Becke with three parameters of Lee-Yang-Parr[ 15 ] and Dunning type aug-cc-pVDZ[ 16 ] basis set, with polarization and diffuse functions, including a function p -polarization in all H atoms. We use the CHELPG[ 17 ] method to describe the partial atomic charges in the molecular force fields in all systems. All energetic values correspond to the lowest energy conformation, which includes zero-point energy correction at the B3LYP/aug-cc-pVDZ calculation level for the neutral and cationic benzene, aniline, o-, m-, and p-nitroaniline. Also, it is determined the topological properties by QTAIM for the electronic structure from the chemical bonds, as electronic density \(\rho \left(r\right)\) , and Laplacian of the electronic density \({\nabla }^{2}\rho \left(r\right),\) given by the Bader's protocol, where some topological parameters regarding the charge concentration in the chemical bonds are defined. For example, Bader defined that when \({\nabla }^{2}\rho \left(r\right)0\) , the sign of the \({\nabla }^{2}\rho \left(r\right)\) indicates the local electronic concentration on a chemical bond, or even at one of the nucleons [ 18 ]. The electronic wavefunction (WFN file) was carried out by Gaussian software (release 09)[ 12 ] and the topological properties were analyzed by the AIMAll package [ 19 ]. Finally, the 2D mapping of the electronic density was obtained by Chemissian software [ 20 ]. 3. Results And Discussion The theoretical calculations of the electronic structure of the BZ, ANI, and NA molecules have shown the effect of double ionization on the chemical bonds of -CC-, -NH 2 , and -NO 2 groups when are removed two electrons from the neutral molecules. The different isomeric conformations lead to the stabilization of the system in the molecular ion doubly ionized (BZ 2+ , ANI 2+ , oNA 2+ , mNA 2+ , and pNA 2+ ), which each molecular ion needs to find a new conformation of lower energy to compensate the loss of two electrons from the system. Figure 1 shows the neutral species for the different structures of the BZ(a), ANI(b), oNA(c), mNA(d), and pNA(e) molecules. They also have different angles between carbon and nitrogen atoms, and in the angle bisector between HNH, when compared to the aniline molecule. The ANI(b), mNA(d) and pNA(e) molecules have the hydrogen facing outside the molecular plane with an angle value of 142.5 o to the aniline molecule, suggesting a hybridization a little closer to the sp 3 to sp 2 [ 21 ]. However, with the effect of double ionization in ANI 2+ (g), mNA 2+ (i), and pNA 2+ (j) molecules the angles will disappear and the hydrogen atoms return to the molecular plane. Now, we can observe a new molecular conformation with the amine group with approximately 90.4 o on the plane of carbon atoms of the aromatic ring. Also, a change in the conformation is observed, and the amine group undergoes an approximate rotation of 38.9 o about the plane of the carbon atoms of the aromatic ring on the mNA 2+ (Fig. 1 (i)). These changes in the structures of nitroanilines occur when there is a change in the isomeric positions. Figure 1 (c) shows the formation of the intramolecular bond between the H⋅⋅⋅O atoms at the 1.906 Å to the neutral molecule, and in the oNA 2+ molecule (h) the distance is reduced to the 1.715 Å. In the oNA neutral and dicationic, the geometry undergoes a small change, within the removal of two electrons from the molecular system. The nitro group in the meta - or para - position is free to rotate around the C-N bond, whilst in the ortho isomeric position, the bond formed by H⋅⋅⋅O is strong enough to keep the system in a single plane. The BZ molecule is flat and symmetrical, unlike BZ 2+ (f) which has two carbon atoms outside the plane, as well as the doubly ionized hydrogen atoms. The effect of double ionization on molecules that have the -NH 2 group causes the hydrogen atoms to be in a single molecular plane. From the results, the angle values of the neutral molecule of oNA are α = 155.90 o , β = 118.19 o , and γ = 118.76 o . While for dicationic molecule the angles values are α' = 115.86 o , β' = 121.18 o and γ' = 116.42 o . Only the neutral or dicationic molecules of oNA (Figs. 1 (c) and 1(h), respectively) do not present any atoms outside of the molecular plane. According to the natural orbital (NBO) [ 22 ], there is a formation of hydrogen bonding between the hydrogen of the -NH2 group and the oxygen of the -NO 2 group. 3.1. Analysis of the Wiberg bond indices and Bader's topology It was analyzed the chemical bonds between C-C, C-N, and N-O of neutral and dicationic molecules using Wiberg bond indices and the quantum theory of atoms in molecules (QTAIM) [ 10 ],[ 11 ], in the search for the weakest bonds and most likely to break to form a possible stable fragments. Molecular ions (M+) show a smaller percentage reduction in bond order and electron density in some bond pairs. This reduction in electron density is evident when molecular structures are studied by computational methods. Table 1 shows the values of the bond length (L), bond order (BO), electronic density \(\rho \left(r\right)\) , Laplacian of the electronic density, \({\nabla }^{2}\rho \left(r\right)\) , and the differences for the bond order (∆ BO ) and electron density (∆ ρ ) for both, neutral and dicationic states of the benzene molecule. The values for the benzene, aniline, and the nitroanilines, in conformations ortho -, meta - and para -, for the neutral and doubly ionized molecules are shown in the supplementary material. Also, it is calculated the percentage of reduction (PR %) in the electronic density of pairs of atoms, when identifying a reduction in electronic density. The Calculation of percentage reduction is performed using Eq. ( 1 ) given below: Table 1 Comparison of bond length (L (Å); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆ ρ ) of benzene molecule neutral and dicationic; and percentage reduction (PR) in the electronic density Exp.[ 38 ] Neutral Dicationic Bond L (Å) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) ∆ BO ∆ ρ PR% r(C1-C2) 1.3971 1.399 1.456 0.304 -0.740 1.464 0.813 0.280 -0.688 0.643 0.025 -7.895 r(C2-C3) 1.3971 1.399 1.455 0.305 -0.740 1.397 1.209 0.301 -0.725 0.246 0.003 -1.311 r(C3-C4) 1.3971 1.399 1.457 0.304 -0.740 1.397 1.209 0.301 -0.725 0.248 0.003 -0.987 r(C4-C5) 1.3971 1.399 1.456 0.304 -0.740 1.464 0.813 0.280 -0.688 0.643 0.025 -7.895 r(C5-C6) 1.3971 1.399 1.455 0.305 -0.740 1.397 1.209 0.301 -0.725 0.246 0.003 -1.311 r(C6-C1) 1.3971 1.399 1.457 0.304 -0.740 1.397 1.209 0.301 -0.725 0.248 0.003 -0.987 CCC ( o ) 120 119.9 123.2-107.2 $$PR\text{%}=\left(\frac{{\rho }_{Dication}}{{\rho }_{Neutral}}-1\right)\times 100$$ 1 Table 1 shows the pairs of atoms r(C1-C2) and r(C4-C5) of the BZ 2+ molecule, which have lower bond order, lower electronic density, and also a percentage of reduction of -7.895%, concerning the neutral molecule. In addition, it is possible to form two types of fragments C 2 H 2 + , and C 3 H 3 + of mass-to-charge ratio m/e = 26, and m/e = 39, respectively. They are potentially favorable fragments, and sufficient to maintain consistency with the experimental results of mass spectrometry of benzene molecule [ 39 – 43 ]. Table 2 shows r(C2-C3), r(C4-C5), r(C5-C6), and r(C7-C2) bond lengths of the ANI and ANI 2+ molecules, which have lower bond order and lower electronic. However, r(C2-C3) and r(C7-C2) bond lengths have a significant percentage of reduction with values around − 11.3%. This percentage is a strong indication of the break bond position with the possibility of formation of the C 5 H 5 + and C 5 H 6 + fragments of the mass-to-charge ratio of m/e = 65 and m/e = 66, respectively. The fragments show consistency with the result found in the literature [ 44 – 46 ]. Table 2 Comparison of bond length (L (Å); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆ ρ ) of aniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density Exp.[ 39 ] Neutral Dicationic Bond L (Å) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) ∆BO ∆ρ PR% r(N1-C2) 1.402 1.400 0.962 0.296 -0.908 1.295 1.542 0.360 -0.703 -0.580 -0.064 21.622 r(C2-C3) 1.397 1.407 0.931 0.301 -0.728 1.485 0.630 0.267 -0.637 0.301 0.035 -11.296 r(C3-C4) 1.394 1.396 1.434 0.305 -0.736 1.361 1.955 0.329 -0.849 -0.521 -0.024 7.869 r(C4-C5) 1.396 1.399 1.439 0.304 -0.736 1.441 1.021 0.288 -0.707 0.418 0.016 -5.263 r(C5-C6) - 1.399 1.439 0.304 -0.736 1.441 1.021 0.288 -0.707 0.418 0.016 -5.263 r(C6-C7) - 1.396 1.434 0.305 -0.736 1.361 1.955 0.329 -0.849 -0.521 -0.024 7.869 r(C7-C2) - 1.407 0.931 0.301 -0.728 1.485 0.630 0.267 -0.637 0.301 0.035 -11.296 HNH (º) 113.10 111.9 115.5 HNC (º) 115.94 115.5 122.2 Table 3. Comparison of bond length (L (Å); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆ BO ); electron density difference (∆ ρ ) of o-nitroaniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density. Exp[ 40 ],[ 41 ] Neutral Dicationic Bond L (Å) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) ∆BO ∆ρ PR% r(N1-C2) 1.455 1.358 1.148 0.322 -1.056 1.290 1.457 0.368 -0.795 -0.309 -0.047 14.286 r(C2-C3) 1.402 1.426 0.102 0.291 -0.686 1.491 0.600 0.265 -0.620 0.960 0.027 -8.935 r(C3-C4) 1.387 1.408 0.90 0.300 -0.723 1.355 0.733 0.333 -0.872 -0.643 -0.033 11.000 r(C4-C5) 1.374 1.383 1.961 0.312 -0.768 1.449 1.305 0.283 -0.687 0.656 0.029 -9.295 r(C5-C6) 1.380 1.409 1.649 0.299 -0.723 1.428 1.302 0.294 -0.730 0.347 0.005 -1.672 r(C6-C7) 1.383 1.383 1.505 0.313 -0.769 1.366 1.756 0.326 -0.842 -0.251 -0.013 4.153 r(C7-C2) 1.379 1.421 0.477 0.294 -0.706 1.488 0.366 0.266 -0.631 0.111 0.029 -9.524 r(C3-N9) 1.451 1.450 0.871 0.266 -0.671 1.507 0.676 0.254 -0.570 0.195 0.012 -4.511 r(N9-O8) 1.217 1.245 0.860 0.494 -1.038 1.235 0.949 0.528 -1.151 -0.890 -0.034 6.883 r(N9-O10) 1.226 1.230 0.914 0.476 -0.976 1.203 1.102 0.488 -0.995 -0.188 -0.011 2.521 HNH (º) - 121.3 121.3 HNO (º) 124.7 122.4 127.4 Table 3 shows r(C2-C3) and r(C4-C5) bond lengths with lower bond order, and r(C2-C3), r(C4-C5), and r(C7-C2) bond lengths with lower electronic density for the neutral and dicationic molecules of oNA. However, the results show a percentage of reduction of -8.935% for r(C2-C3), -9.295% for r(C4-C5), and − 9.524% for r(C7-C2). There is possibility of formation of C 6 H 6 N + and C 5 H 6 + fragments of mass-to-charge ratio of m/e = 92 and m/e = 66, respectively. The fragments show consistency with the result found in the literature [ 23 ],[ 24 ]. Table 4 shows r(C2-C3), r(C5-C6), and r(C7-C2) bond lengths with lower bond order, and r(C2-C3) and r(C7-C2) bond lengths with lower electronic density for the neutral and dicationic molecules of mNA2+. There are two bond lengths with a significant percentage of reduction of -9.603% for r(C2-C3) and − 11.296% for r(C7-C2). There is possibility of formation of C 5 H 5 + , C 6 H 6 N + , and C 5 H 6 N + fragments of mass-to-charge ratio of m/e = 65, m/e = 80 and m/e = 92, respectively. The fragments show consistency with the result found in the literature [ 24 ],[ 25 ]. Table 4 Comparison of bond length (L (Å); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆ ρ ) of m-nitroaniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density Exp.[ 2 ] Neutral Dicationic Bond L (Å) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) ∆BO ∆ρ PR% r(N1-C2) 1.380 1.392 0.949 0.302 -0.942 1.301 1.465 0.357 -0.773 -0.516 -0.055 18.212 r(C2-C3) - 1.405 1.329 0.302 -0.731 1.468 0.828 0.273 -0.651 0.501 0.029 -9.603 r(C3-C4) - 1.393 0.551 0.308 -0.752 1.356 1.218 0.331 -0.850 -0.667 -0.024 7.468 r(C4-C5) - 1.395 0.526 0.307 -0.755 1.441 0.678 0.290 -0.714 -0.152 0.018 -5.538 r(C5-C6) - 1.397 1.792 0.304 -0.737 1.430 1.288 0.292 -0.721 0.504 0.012 -3.947 r(C6-C7) - 1.395 1.562 0.306 -0.742 1.366 1.848 0.325 -0.837 -0.286 -0.020 6.209 r(C7-C2) - 1.410 1.109 0.301 -0.728 1.486 0.648 0.267 -0.635 0.461 0.034 -11.296 r(C4-N9) 1.457 1.479 0.657 0.254 -0.623 1.483 0.703 0.265 -0.654 -0.460 -0.011 4.331 r(N9-O8) 1.222 1.230 0.869 0.496 -1.051 1.203 1.125 0.490 -1.019 -0.256 0.006 -1.210 r(N9-O10) 1.221 1.228 0.804 0.495 -1.045 1.235 1.027 0.526 -1.131 -0.223 -0.031 6.263 HNH (o) 114.6 113.0 115.5 HNO (o) 122.8 124.3 128.9 Table 5 shows r(C2-C3), r(C3-C4), r(C6-C7), r(C7-C2), and r(C5-N9 ) bond lengths with lower bond order, and r(C2-C3), r(C4-C5), r(C5-C6), r(C7-C2) and r(N9-O10) bond lengths with lower electronic density for the neutral and dicationic molecules of pNA 2+ . There are five bond lengths with a significant percentage of reduction of -9.030% for r(C2-C3), -7.213% for r(C4-C5), -7.213% for r(C5-C6), -9.030% for r(C7-C2), and 4.684% for r(N9-O10). There is possibility of formation of C 5 H 6 N + , C 6 H 6 N + +, and C 6 H 5 NO + fragments with mass-to-charge ratio of m/e = 80, m/e = 92, and m/e = 107, respectively. The fragments show consistency with the result found in the literature [ 24 ],[ 26 ],[ 27 ]. Table 5 Comparison of bond length (L (Å); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆ ρ ) of p-nitroaniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density Exp.[ 2 ] Neutral Dicationic Bond L (Å) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) L (Å) BO \(\rho\) (1/𝑎03) \({\nabla }^{2}\rho\) (1/𝑎05) ∆BO ∆ρ PR% r(N1-C2) 1.355 1.380 1.064 0.307 -0.978 1.301 1.458 0.357 -0.795 -0.394 -0.050 16.287 r(C2-C3) - 1.413 1.066 0.299 -0.722 1.474 0.845 0.272 -0.651 0.221 0.027 -9.030 r(C3-C4) - 1.388 2.204 0.309 -0.751 1.356 1.977 0.330 -0.842 0.227 -0.021 6.796 r(C4-C5) - 1.399 0.482 0.305 -0.746 1.445 0.908 0.283 -0.686 -0.426 0.022 -7.213 r(C5-C6) - 1.399 0.482 0.305 -0.746 1.445 0.908 0.283 -0.686 -0.426 0.022 -7.213 r(C6-C7) - 1.388 2.204 0.309 -0.751 1.356 1.977 0.330 -0.842 0.227 -0.021 6.796 r(C7-C2) - 1.413 1.066 0.299 -0.722 1.474 0.845 0.272 -0.651 0.221 0.027 -9.030 r(C5-N9) 1.433 1.459 0.753 0.264 -0.671 1.453 0.454 0.279 -0.765 0.299 -0.015 5.682 r(N9-O8) 1.244 1.233 0.861 0.491 -1.027 1.181 1.413 0.550 -1.233 -0.552 -0.059 12.016 r(N9-O10) 1.235 1.233 0.861 0.491 -1.027 1.254 1.056 0.468 -0.928 -0.195 0.023 -4.684 HNH (o) 120.9 114.9 115.6 HNO (o) 122 123.9 132.9 There was a significant increase in the bond order in the dicationic states in relation to the isomeric positions of the r(N1-C2) bond length, following the order: oNA 2+ (26.92%) < pNA 2+ (45.8%) oNA 2+ (-22.4%). However, there is an increase in the bond order of pNA 2+ (7%) due to charge relocation which can be favorable to the electron transfer by the -NO 2 group in the pNA 2+ . Therefore, the best relocation of charge is an indication of an increase in the bond order[ 28 ]. The electron transfer possibility an analysis from this first analysis based on electrostatic potential maps can relate the changes in the bond order, the electronic density, and positive/negative regions. The electrostatic potential map (PES) [ 29 ] is a tool used to determine the reactive regions of nucleophilic and electrophilic attacks in a molecular system. Figure 2 shows the map of the potential energy surface generated by the electron isodensity surface of 0.02/a.u3 for each point on the map for the molecules of BZ, ANI, oNA, mNA, and pNA. Thereby, the increase in bond orders of the -NH2 group, and the reduction of bond orders for the group -NO 2 can be analyzed with help of electrostatic potential maps from the electrostatic interactions between species doubly ionized. These areas of electrostatic potentials can be displayed as isocontour surfaces (maps of electron density). The electrostatic potential maps of neutral and dicationic molecules indicate a lower charge concentration in all dications, mainly in the dark blue regions, justified by the decrease in the -NH 2 group bond order. The regions of positive electrostatic potential are concentrated mainly on the nitrogen atoms of the amine group and also on the hydrogen atoms. The dark blue and light blue areas represent a positive potential of atoms -H bond to the nitrogen and ring carbon atoms. However, due to the influence of the -NO 2 group, which determines the character of a negative charge, this potential map is changed and these changes are represented in the regions in red, negative potential. The loss of two electrons in the (f), (g), (h), (i), and (j) monomers; leaving the peripheral regions to the center of the ring more positive (surface observed in dark blue and light blue) toward the center of the ring for bonds with lower bond order. The electron-donating groups, such as the -NH 2 , increase the electron density in the positions ortho- , meta- , and para- in an aromatic of the Kekulé's circuits type[ 30 ] (electron-withdrawing groups). Wiberg's binding indices and Bader's topological analysis satisfactorily describe the weaker connections of molecular systems in the studies. In the comparison of the results found by both theories, it was necessary to define the connections with lower charge concentrations, with greater possibilities of breaking chemical bonds. In order to do this, electronic density maps and the Laplacian electronic density (topological analysis), show curves, and regions of higher concentrations of charge on the bonds in the layer of valence [ 31 ]. The electronic densities are located in pairs of atoms showing higher and lower concentrations of charge, especially in the regions probable to break bonds at the dications. The pairs of atoms that have connected regions have higher concentrations of load on the bonds and are less likely to break the bond in these regions [ 32 ]. From Fig. 3 , it is possible to observe the different concentrations of charge. The BZ molecule (a) shows concentrations of uniform charges throughout its structure, but the BZ 2+ molecule (C) shows a low concentration of charge (or lower electronic density) in the r(C1-C2), and r(C4-C5) bond lengths. The ANI molecule (b) removes the uniformity of density in the aromatic ring due to group -NH 2 . The change in the electronic density of ANI 2+ molecule (d) shows a difference between the electronic densities in the r(C2-C3), r(C4-C5), r(C5-C6), and r(C7-C2) bond lengths. At the top of Fig. 4 , the neutral states of the oNA (a), mNA (b), and pNA (c) molecules are shown. The oNA (a) molecule presents intramolecular interaction between the oxygen from the nitro group and the hydrogen from the amino group, which indicates that the nuclei support all concentrations of charge ( \({\nabla }^{2}\rho \left(r\right)\) > 0). Whilst, oNA 2+ molecule (d) shows a significant increase in the electronic density in the region of interaction H⋅⋅⋅O(8)-, and a lower electronic density in the r(C2-C3), r(C4-C5), r(C7-C2), and r(C3-N9) bond lengths. The mNA 2+ (e) and pNA 2+ (f) molecules show the lower concentrations of charge in r(C2-C3), r(C4-C5), r(C5-C6), r(C7-C2), and r(N9-O8) bond lengths in relation to the neutral molecule. Therefore, with the relaxation of the system, the charge distribution is altered, thus leaving some pairs of atoms weaker than the others and this can be seen in the electronic density maps, represented graphically for neutral and doubly ionized species. Even though, the possibility to find a route of fragmentation by the reduction of the electronic densities (using Bader’s protocol) of chemical bonds in molecule dicationics, not all pairs of atoms involved in this analysis converge to the result of the analysis in terms of the bond orders. Therefore, the use of both methods to estimate the chemical bonds are necessary. 3.2. Thermodynamic properties In addition, we approach the thermodynamic properties of each neutral and doubly ionized molecular structure and mix it with other results found in the literature, to assemble Table 6 , which was very useful in the construction of Table 7 , where the results of the enthalpy calculations are found. formation at temperatures of 0K and 298K, and Gibbs free energy. Table 6 Standard enthalpy of formation of neutral elements ( Δ Ho), Standard enthalpy of formation at 0K, and entropy at 298K of the cationic elements ( Δ fHo in kcal.mol-1 and ΔSo in kcal.mol-1K-1, respectively) Neutral ΔHo [a] ion ΔfHo (X,0K) ΔSo(X,298K) H 1.01 H+ 365.20[b] 26.012 C 0.25 C+ 429.60[c] 34.773 N 1.04 N+ 447.60[d] 33.856 O 1.04 O+ 373.04[e] 35.629 [a] ref.[ 33 ]; [b] Ref.[ 42 ]; [c] Ref.[ 34 ]; [d] Ref.[ 43 ]; [e] Ref.[ 44 ] Table 7 Molecular ions, doubly ionized, atomic mass unit (amu), fragmentation channels, and the enthalpy of formation (0K and 298K) and their Gibbs free energies (kcal.mol − 1). Neutral molecule Mass (amu) ∆ Ho(0k) ∆ Ho(298k) ∆ Go(298k) BZ C6H62+ 78 559.9 556.1 645.0 ANI C6H5NH2+ 93 423.9 418.6 592.4 ONA C6H6N2O2 + 2 138 181.7 175.8 636.9 MNA C6H6N2O2 + 2 138 175.0 169.3 635.0 PNA C6H6N2O2 + 2 138 168.0 162.3 630.3 In Table 6 we present the ions: hydrogen (H + ), carbon (C + ), nitrogen (N + ), and oxygen (O + ), with the combination of thermodynamic properties of enthalpies formation of neutral elements (H 298K -H 0K ) with the enthalpies of formation of the cationic atoms and between the calculated entropies of each ion ( S o 298K ), seeking a better approximation of the energy properties of the molecular ions listed in Table 7 . But, to generate each value enthalpy of formation ( \(\varDelta {H}_{0K}^{o}\) and \(\varDelta {H}_{298K}^{o}\) ) and Gibbs free energy ( \(\varDelta {G}_{298K}^{o}\) ). The Eq. ( 2 ) represents the enthalpy of formation in 0K, where x is the number of atoms of X that represents each element of a molecule M, and ∑D o (M) represents the atomization energy of the molecule (M). $${\varDelta }_{f}{H}_{0K}^{o}=\sum _{atoms}x{\varDelta }_{f}{H}_{(X;0K)}^{o}-\sum _{atoms}{D}_{o}\left(M\right)$$ 2 Equation ( 3 ) represents the enthalpy of formation in 298K, where \({H}_{M}^{o}\left(298K\right)-{H}_{M}^{o} \left(0K\right)\) represents the correction of the enthalpy for the molecule M, and \({H}_{X}^{o}\left(298K\right)-{H}_{X}^{o}\left(0K\right)\) is the correction of the enthalpy of atomic elements X. $${\varDelta H}_{298 K}^{o}={\varDelta H}_{0 K}^{o}+\left[{\varDelta H}_{M}^{o} \left(298K\right)-{\varDelta H}_{M}^{o} \left(0K\right)\right]$$ $$-\sum x\left[{\varDelta H}_{M}^{o} \right(298K)-{\varDelta H}_{M}^{o} (0K\left)\right]$$ 3 The Eq. ( 4 ) represents the Gibbs free energy in 298K, where \({S}_{(M, 298K)}^{o}\) and \({S}_{(X, 298K)}^{o}\) represent the enthalpy of reaction of the molecule M, the entropy of atoms. $$\varDelta {G}_{298K}{H}_{0K}^{o}={\varDelta }_{r}{H}_{\left(298K\right)}^{o}-298.15({S}_{(M,298K)}^{o}-\sum {S}_{(x,298K)}^{o})$$ 4 The equations ( 2 ), ( 3 ), and (4) were used to calculate the assemble in Table 7 , based on the References [ 33 ], [ 34 ] and [ 35 ]. We present in Table 7 the doubly ionized molecular ions of benzene, aniline, and nitroaniline (ortho, meta, and para), accompanied by their atomic masses of its enthalpies of formation in 0K, and 298K; and their Gibbs free energies. For positive energies, we have a non-spontaneous process, due to the removal of two electrons of the system requiring a large amount of energy (Ionization Potential - IP ) for which the electrons are ejected out of the layer of the valence of the molecule. However, we found a paper that refers to the heat of formation of benzene doubly ionized experimental value of 26.0 eV = 599.57 kcal.mol-1 [ 36 ]. From the values of ground state energy of the systems, it was possible to calculate the IP of the structures using Eq. (5) [ 37 ]. IP = E N−1 - E N (5) Where E (N−1) and E N are the total energies of the (N-1) and N electron system, respectively. Table 8 shows the values of electronic energy (E 0 ), dipole moment ( µ ), and ionization potential ( IP ), of neutral molecules, and dicationics; and compare them with some experimental results found in the literature. The results show a good approximation of our theoretical calculations with experimental results, revealing that the neutral molecules have theoretical results of the dipole moment of ionization potential, and are very close to the experimental results. Table 8 Dipole moments (µ) and ionization potential (IP) for neutral and dicationic chemical species at the UB3LYP/aug-cc-pVDZ calculation level, and experimental values found in the literature. Molecules Theoretical Exp. E T (a.u) µ [D]* IP (eV) µ [D]* IP (eV) Neutral BZ -232.27460349 0.0 9.1 0.0[a] 9.24[c] ANI -287.64377206 1.6 7.5 1.5[b] 7.72[d] ONA -492.18807246 4.9 8.2 4.3[b] 8.43[e] MNA -492.18374531 5.8 8.2 4.9[b] 8.60[f] PNA -492.18774648 7.4 8.3 6.2[b] 8.43[f] Dicationic BZ2+ -231.37763151 0.0 21.3 - - ANI2+ -286.86572780 2.8 20.3 - - ONA2+ -491.36806291 10.1 19.8 - - MNA2+ -491.36709206 12.5 19.4 - - PNA2+ -491.37881464 10.8 20.2 - - [D]* = 1 Debye = 3.33564 x 10–30 C.m [a] ref.[ 45 ]; [b] Ref.[ 46 ]; [c] Ref.[ 47 ]; [d] Ref.[ 48 ]; [e] Ref.[ 49 ]; [f] Ref.[ 50 ]. Conclusion The investigation of a theoretical molecular fragmentation route may be possible through the application of two methods: Wiberg's bond indexes and Bader’s topological analysis (QTAIM). In addition, the electrostatic potential maps, indicate the most positive areas of the molecules that coincide with the reduction in electronic densities. After careful analysis of the obtained results, such as bond length, bond order, and electronic density, we verified that these methodologies take to the same conclusion as our previous analysis for the BZ 2+ case, which has two sigma bonds, with smaller bond orders, and more positive areas in the proximities of the ligands of smaller electronic densities, and the possibility to form fragments of the type C 3 H 3 + , and C 2 H 2 + . The ANI 2+ possesses four ligands with smaller bond orders, more positive areas in the proximities of the ligands with a percentage reduction in the electronic densities, and the possibility to form fragments of the type C 5 H 5 + , and C 5 H 6 + . The oNA 2+ presents five ligands with smaller bond orders, more positive areas in the proximities of the ligands of percentage reduction in the electronic densities, and the possibility of forming fragments of the type C 5 H 6 + , and C 6 H 6 + . The mNA 2+ has three ligands with lower binding orders and more positive areas in the vicinity of the ligands, and present percentage reduction in the electronic densities with the possibility to form fragments of the type C 5 H 5 + , C 5 H 6 N + , and C 6 H 6 N + . The pNA2 + presents the ligands r(C4-C5) and r(C5-C6) as being the main ligands involved in the formation of the fragments C 5 H 5 +, C 5 H 6 N +, and C 6 H 6 N + , but, it has more than four ligands with smaller orders and more positive areas in the vicinity of the ligands, a percentage reduction in electronic densities. We verified that the process of charge transfer and electronic distribution in the nitroanilines occurs in the area of the group -NO 2 . The donor or acceptor of the electrons groups changes the percentage of the density, and the bond order, as in the case of the pairs of atoms at isomeric positions. Generating like this, π bonds of the low bond index, and electronic delocalization in the ring of the neutral system, as seen previously in Fig. 4 of the electrostatic maps of surfaces of potential energy. Still, in the result of our analyses of QTAIM, it was revealed that the largest densities of charges are located in the group -NH 2 of the dications, and the smallest densities of charges in the groups C-NH 2 , and -NO 2 , start a possible process of molecular fragmentation in the dicationic nitroanilines. Thus, we conclude that both methodologies applied in the investigation of a fragmentation route lead to the indication of weakened bonds due to the removal of two electrons from the system, it may be due to the reduction of the order of the bonds or by the percentage reduction in the electronic density. Abbreviations oNA ortho- Nitroanilines mNA meta- Nitroanilines pNA para-Nitroanilines BZ Benzene ANI Aniline NA Nitroanilines Declarations Declaration of Competing Interest The authors declare that there is no conflict of interests regarding the publication of this research paper. Authorship contribution statement Ms. Carlos Xavier de Oliveira : Conceptualization, Investigation, Methodology, Visualization, Writing-original draft. Dr. Fabio L P Costa : Data curation, Writing-review editing. Dr. Gunar V S Mota : Visualization, Writing-review editing. Acknowledgments This work has been financially supported by CAPES for providing post-graduate scholarship and the Institute of Physics, University of Brasília (UnB). In memory of Dra. Maria Suely P. Mundin (UnB). Funding Data availability Not applicable. Code availability Not applicable. Ethicsapproval Not applicable. Consent to participate Not applicable. Consent for publication All the authors gave their consent for publication. 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Journal of the Chemical Society, Faraday Transactions 2. 69 , 36–42 (1973). https://doi.org/10.1039/f29736900036 Additional Declarations No competing interests reported. Supplementary Files floatimage1.jpg Cite Share Download PDF Status: Published Journal Publication published 26 Jan, 2023 Read the published version in Journal of Molecular Modeling → Version 1 posted Editorial decision: Major revision 22 Aug, 2022 Reviews received at journal 16 Aug, 2022 Reviewers agreed at journal 25 Jul, 2022 Reviewers invited by journal 20 Jul, 2022 Editor assigned by journal 15 Jul, 2022 Submission checks completed at journal 15 Jul, 2022 First submitted to journal 04 Jul, 2022 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-1825286","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":121253261,"identity":"4d57eb83-6fae-4b83-a9d4-dc3658752f6e","order_by":0,"name":"Carlos X. 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Mota","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAqElEQVRIiWNgGAWjYNCCCgZ+IMlGipYzDJINpGlhbCNFi3xE7sHPlfMOS5izH2B7XEGMFsMbecmSZ7cdlrDsSWA3PEOUlhk5BpKN2w7XGRxIYAO5jigtxj8b5xyWMDj/gEgt8hI5ZpKNDUAtN4i1xYDnjZllw7F0CcsZD9sNibOlPcf4ZkONtYQ5f/Kxh8TZcgDGYGAkSgPQFpg6A+LUj4JRMApGwUgEALJzMQbxuIGXAAAAAElFTkSuQmCC","orcid":"","institution":"UFPA","correspondingAuthor":true,"submittingAuthor":false,"prefix":"","firstName":"Gunar","middleName":"V. S.","lastName":"Mota","suffix":""}],"badges":[],"createdAt":"2022-07-05 00:44:08","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-1825286/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-1825286/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1007/s00894-023-05461-3","type":"published","date":"2023-01-26T18:32:52+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":24213203,"identity":"daaf4223-441c-46a4-b4ef-9fb92ecc854c","added_by":"auto","created_at":"2022-07-22 17:45:28","extension":"jpeg","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":346289,"visible":true,"origin":"","legend":"\u003cp\u003eNeutral (a)-(e) and dications (f)-(j) molecules of benzene, aniline and o-, m- and p-nitroanilines. The bond length magnitudes in Angstroms of the molecules are indicated, as well as the alpha (α), beta (β), and gamma (γ) angles in o-nitroaniline.\u003c/p\u003e\u003cp\u003e\u003cbr\u003e\u003c/p\u003e","description":"","filename":"floatimage2.jpeg","url":"https://assets-eu.researchsquare.com/files/rs-1825286/v1/e8bbfb2f2d34509cdcde0a8d.jpeg"},{"id":24214501,"identity":"1a5d13e5-5a08-410f-89f0-2870b68769bd","added_by":"auto","created_at":"2022-07-22 17:55:28","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":460167,"visible":true,"origin":"","legend":"\u003cp\u003eElectrostatic potential maps (plotted on an isodensity surface = 0.02/a.u\u003csup\u003e3\u003c/sup\u003e) for a class of neutral molecules in the first Table: BZ (a), ANI (b), ONA (c), MNA (d), PNA (e), and the same class of molecules in the second Table, but now doubly ionized: BZ (f), ANI (g), ONA (h), MNA (i), PNA (j).\u003c/p\u003e\u003cp\u003e\u003cbr\u003e\u003c/p\u003e","description":"","filename":"floatimage3.png","url":"https://assets-eu.researchsquare.com/files/rs-1825286/v1/97a5cdcde54dd2877407caea.png"},{"id":24213207,"identity":"2984bf99-8a6c-41e8-bd0f-3ca5eafc553d","added_by":"auto","created_at":"2022-07-22 17:45:28","extension":"jpg","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":138086,"visible":true,"origin":"","legend":"\u003cp\u003eElectronic density maps in the plane of atoms from -C-C- to a) BZ, c) BZ\u003csup\u003e2+\u003c/sup\u003e; and also electronic density maps in the N-C and -C-C- plane for b) ANI, d) ANI\u003csup\u003e2+\u003c/sup\u003e. Units are reciprocal cubic angstrom (1/Å\u003csup\u003e3\u003c/sup\u003e). Isodensity color pattern is the same for both conformer types.\u003c/p\u003e\u003cp\u003e\u003cbr\u003e\u003c/p\u003e","description":"","filename":"Fig3.jpg","url":"https://assets-eu.researchsquare.com/files/rs-1825286/v1/4613456c9f605419fb6a67d5.jpg"},{"id":24213204,"identity":"215a7f15-ed18-4037-8cbd-50279f1d4535","added_by":"auto","created_at":"2022-07-22 17:45:28","extension":"jpg","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":171373,"visible":true,"origin":"","legend":"\u003cp\u003eElectronic density maps in the plane of the atoms N-C, -C-C- and O=N=O for nitroanilines in e) ONA, h) ONA\u003csup\u003e2+\u003c/sup\u003e; f) MNA, i) MNA\u003csup\u003e2+\u003c/sup\u003e; and g) PNA, j) PNA\u003csup\u003e2+\u003c/sup\u003e. Units are reciprocal cubic angstrom (1/Å\u003csup\u003e3\u003c/sup\u003e). Isodensity color pattern is the same for both conformer types.\u003c/p\u003e\u003cp\u003e\u003cbr\u003e\u003c/p\u003e","description":"","filename":"Fig4.jpg","url":"https://assets-eu.researchsquare.com/files/rs-1825286/v1/6d8b8f82a6e3d61d4324fc7e.jpg"},{"id":44717740,"identity":"0fe36cbc-2790-4476-a421-2183e1e6cc77","added_by":"auto","created_at":"2023-10-16 18:39:27","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":1564858,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-1825286/v1/36164e20-e54d-4ac4-bbf0-1e5c25eb2587.pdf"},{"id":24214089,"identity":"54e7462b-0707-439a-b56e-07f7279cc361","added_by":"auto","created_at":"2022-07-22 17:50:28","extension":"jpg","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":670408,"visible":true,"origin":"","legend":"","description":"","filename":"floatimage1.jpg","url":"https://assets-eu.researchsquare.com/files/rs-1825286/v1/bf32402b7833ef5864e39159.jpg"}],"financialInterests":"No competing interests reported.","formattedTitle":"Fragmentation Route of doubly ionized benzene, aniline, and nitroanilines monomers using a novel protocol from density functional theory and QTAIM","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eThe studies of mass spectrometry are focused on the analysis of the fragmentation of species present in the ionosphere of extraterrestrial planets that, in their states of charge 2+ (doubly charged), which suggests a possible way of molecular fragmentation, formed by pairs of atoms in molecules of the same chemical species, but in different charge states [\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eMolecules, such as benzene, which in its gaseous phase have an aromatic ring with amine, and nitro groups in your structure, are known as push-pull molecules, characterized by groups of donors and acceptors of electrons between \u003cem\u003epi\u003c/em\u003e-conjugated bonds [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e],[\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e]. In recent studies of time-of-flight mass spectrometry (TOF), double-ionized benzene monomer was observed in dissociative processes, when excited by synchrotron radiation [\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e]. These stable nitroaromatic fragments have significant concentrations of charges (or electron densities), which can form a metastable state [\u003cspan additionalcitationids=\"CR6 CR7\" citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e]. The systems formed by benzene clusters, doubly ionized, are based on the cationic benzene dimer [C6H6]\u003csup\u003e2+\u003c/sup\u003e, and the dicationic benzene monomer in the C6H6\u003csup\u003e2+\u003c/sup\u003e. They exhibit structural patterns from a variety of low-energy conformations of the cation benzene dimer and dicationic benzene [\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eThe nitroanilines are the simpler examples of molecules with highly polar regions, which are constituted by the aromatic fragment of the electrons group's donors, and acceptors. The absorption spectra of the electronic transitions of aromatic molecules (nitroanilines) were studied. Moreover, the aromatic molecules that have electron acceptor groups -NO\u003csub\u003e2\u003c/sub\u003e, show a stronger absorption, associated with the intramolecular charge transfer, in the region of ultraviolet [\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e],[\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e]. The theoretical results provide a reasonable framework for the interpretation of the complex structure of the spectrum of \u003cem\u003epara\u003c/em\u003e-nitroaniline and the major differences in the spectrum of \u003cem\u003emeta\u003c/em\u003e-nitroaniline [\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e]. The new techniques of elucidation of the formation of molecular fragments for different chemical species lead to the emergence of different forms of theoretical methodology to study the fragmentation of benzene, aniline, and \u003cem\u003eortho\u003c/em\u003e-, \u003cem\u003emeta\u003c/em\u003e- and \u003cem\u003epara\u003c/em\u003e-nitroaniline [\u003cspan additionalcitationids=\"CR14 CR15 CR16 CR17 CR18 CR19\" citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eTo connect the theory to the experiment, we calculated the electronic structure of the molecules, using a new protocol[\u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e] applied to benzene (BZ), aniline (ANI), and the nitroanilines (NA) in conformations \u003cem\u003eortho\u003c/em\u003e-, \u003cem\u003emeta\u003c/em\u003e- and \u003cem\u003epara\u003c/em\u003e- (named oNA, mNA, and pNA, respectively) for the neutral and doubly ionized molecules to understand the dynamics of fragmentation of these molecules. But, to achieve this, we evaluate the bond order by Wiberg's bond index to identify the probable places of bonds break [\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e], and also we had made an analysis of the density of electronics on the bonds by Quantum Theory of Atoms In Molecules (QTAIM) to distinguish the different concentrations of charge in pairs of atoms [\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e].\u003c/p\u003e"},{"header":"2. Methodology","content":"\u003cp\u003eAll our calculations of first principles were performed using the Gaussian software (release 09)[\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e] applied to the molecular structure of the benzene, aniline, o-, m-, and p-nitroaniline, at different levels (neutrals, and ions), the existing basic formalism of Density Functional Theory (DFT) method [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e][\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e], with a B3LYP hybrid functional introduced by Becke with three parameters of Lee-Yang-Parr[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e] and Dunning type aug-cc-pVDZ[\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e] basis set, with polarization and diffuse functions, including a function \u003cem\u003ep\u003c/em\u003e-polarization in all H atoms. We use the CHELPG[\u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e] method to describe the partial atomic charges in the molecular force fields in all systems. All energetic values correspond to the lowest energy conformation, which includes zero-point energy correction at the B3LYP/aug-cc-pVDZ calculation level for the neutral and cationic benzene, aniline, o-, m-, and p-nitroaniline.\u003c/p\u003e \u003cp\u003eAlso, it is determined the topological properties by QTAIM for the electronic structure from the chemical bonds, as electronic density \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho \\left(r\\right)\\)\u003c/span\u003e\u003c/span\u003e, and Laplacian of the electronic density \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho \\left(r\\right),\\)\u003c/span\u003e\u003c/span\u003e given by the Bader's protocol, where some topological parameters regarding the charge concentration in the chemical bonds are defined. For example, Bader defined that when \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho \\left(r\\right)\u0026lt;0\\)\u003c/span\u003e\u003c/span\u003e, there is a larger charge concentration on BCPs (critical points of the chemical bonds); on the other hand, when\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({ \\nabla }^{2}\\rho \\left(r\\right)\u0026gt;0\\)\u003c/span\u003e\u003c/span\u003e, the sign of the \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho \\left(r\\right)\\)\u003c/span\u003e\u003c/span\u003e indicates the local electronic concentration on a chemical bond, or even at one of the nucleons [\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e]. The electronic wavefunction (WFN file) was carried out by Gaussian software (release 09)[\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e] and the topological properties were analyzed by the AIMAll package [\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e]. Finally, the 2D mapping of the electronic density was obtained by Chemissian software [\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e].\u003c/p\u003e"},{"header":"3. Results And Discussion","content":"\u003cp\u003eThe theoretical calculations of the electronic structure of the BZ, ANI, and NA molecules have shown the effect of double ionization on the chemical bonds of -CC-, -NH\u003csub\u003e2\u003c/sub\u003e, and -NO\u003csub\u003e2\u003c/sub\u003e groups when are removed two electrons from the neutral molecules. The different isomeric conformations lead to the stabilization of the system in the molecular ion doubly ionized (BZ\u003csup\u003e2+\u003c/sup\u003e, ANI\u003csup\u003e2+\u003c/sup\u003e, oNA\u003csup\u003e2+\u003c/sup\u003e, mNA\u003csup\u003e2+\u003c/sup\u003e, and pNA\u003csup\u003e2+\u003c/sup\u003e), which each molecular ion needs to find a new conformation of lower energy to compensate the loss of two electrons from the system.\u003c/p\u003e\n\u003cp\u003eFigure\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e shows the neutral species for the different structures of the BZ(a), ANI(b), oNA(c), mNA(d), and pNA(e) molecules. They also have different angles between carbon and nitrogen atoms, and in the angle bisector between HNH, when compared to the aniline molecule. The ANI(b), mNA(d) and pNA(e) molecules have the hydrogen facing outside the molecular plane with an angle value of 142.5\u003csup\u003eo\u003c/sup\u003e to the aniline molecule, suggesting a hybridization a little closer to the \u003cem\u003esp\u003c/em\u003e\u003csup\u003e3\u003c/sup\u003e to \u003cem\u003esp\u003c/em\u003e\u003csup\u003e2\u003c/sup\u003e [\u003cspan class=\"CitationRef\"\u003e21\u003c/span\u003e].\u003c/p\u003e\n\u003cp\u003eHowever, with the effect of double ionization in ANI\u003csup\u003e2+\u003c/sup\u003e(g), mNA\u003csup\u003e2+\u003c/sup\u003e(i), and pNA\u003csup\u003e2+\u003c/sup\u003e(j) molecules the angles will disappear and the hydrogen atoms return to the molecular plane. Now, we can observe a new molecular conformation with the amine group with approximately 90.4\u003csup\u003eo\u003c/sup\u003e on the plane of carbon atoms of the aromatic ring. Also, a change in the conformation is observed, and the amine group undergoes an approximate rotation of 38.9\u003csup\u003eo\u003c/sup\u003e about the plane of the carbon atoms of the aromatic ring on the mNA\u003csup\u003e2+\u003c/sup\u003e (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e(i)). These changes in the structures of nitroanilines occur when there is a change in the isomeric positions.\u003c/p\u003e\n\u003cp\u003eFigure\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e (c) shows the formation of the intramolecular bond between the H\u0026sdot;\u0026sdot;\u0026sdot;O atoms at the 1.906 \u0026Aring; to the neutral molecule, and in the oNA\u003csup\u003e2+\u003c/sup\u003e molecule (h) the distance is reduced to the 1.715 \u0026Aring;. In the oNA neutral and dicationic, the geometry undergoes a small change, within the removal of two electrons from the molecular system. The nitro group in the \u003cem\u003emeta\u003c/em\u003e- or \u003cem\u003epara\u003c/em\u003e- position is free to rotate around the C-N bond, whilst in the ortho isomeric position, the bond formed by H\u0026sdot;\u0026sdot;\u0026sdot;O is strong enough to keep the system in a single plane. The BZ molecule is flat and symmetrical, unlike BZ\u003csup\u003e2+\u003c/sup\u003e(f) which has two carbon atoms outside the plane, as well as the doubly ionized hydrogen atoms. The effect of double ionization on molecules that have the -NH\u003csub\u003e2\u003c/sub\u003e group causes the hydrogen atoms to be in a single molecular plane. From the results, the angle values of the neutral molecule of oNA are \u0026alpha;\u0026thinsp;=\u0026thinsp;155.90\u003csup\u003eo\u003c/sup\u003e, \u0026beta;\u0026thinsp;=\u0026thinsp;118.19\u003csup\u003eo\u003c/sup\u003e, and \u0026gamma;\u0026thinsp;=\u0026thinsp;118.76\u003csup\u003eo\u003c/sup\u003e. While for dicationic molecule the angles values are \u0026alpha;\u0026apos; = 115.86\u003csup\u003eo\u003c/sup\u003e, \u0026beta;\u0026apos; = 121.18\u003csup\u003eo\u003c/sup\u003e and \u0026gamma;\u0026apos; = 116.42\u003csup\u003eo\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003eOnly the neutral or dicationic molecules of oNA (Figs. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e(c) and 1(h), respectively) do not present any atoms outside of the molecular plane. According to the natural orbital (NBO) [\u003cspan class=\"CitationRef\"\u003e22\u003c/span\u003e], there is a formation of hydrogen bonding between the hydrogen of the -NH2 group and the oxygen of the -NO\u003csub\u003e2\u003c/sub\u003e group.\u003c/p\u003e\n\u003cdiv class=\"Section2\" id=\"Sec4\"\u003e\n \u003ch2\u003e3.1. Analysis of the Wiberg bond indices and Bader\u0026apos;s topology\u003c/h2\u003e\n \u003cp\u003eIt was analyzed the chemical bonds between C-C, C-N, and N-O of neutral and dicationic molecules using Wiberg bond indices and the quantum theory of atoms in molecules (QTAIM) [\u003cspan class=\"CitationRef\"\u003e10\u003c/span\u003e],[\u003cspan class=\"CitationRef\"\u003e11\u003c/span\u003e], in the search for the weakest bonds and most likely to break to form a possible stable fragments. Molecular ions (M+) show a smaller percentage reduction in bond order and electron density in some bond pairs. This reduction in electron density is evident when molecular structures are studied by computational methods.\u003c/p\u003e\n \u003cp\u003eTable \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e shows the values of the bond length (L), bond order (BO), electronic density \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho \\left(r\\right)\\)\u003c/span\u003e\u003c/span\u003e, Laplacian of the electronic density, \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho \\left(r\\right)\\)\u003c/span\u003e\u003c/span\u003e, and the differences for the bond order (∆\u003cem\u003eBO\u003c/em\u003e) and electron density (∆\u003cem\u003e\u0026rho;\u003c/em\u003e) for both, neutral and dicationic states of the benzene molecule. The values for the benzene, aniline, and the nitroanilines, in conformations \u003cem\u003eortho\u003c/em\u003e-, \u003cem\u003emeta\u003c/em\u003e- and \u003cem\u003epara\u003c/em\u003e-, for the neutral and doubly ionized molecules are shown in the supplementary material. Also, it is calculated the percentage of reduction (PR %) in the electronic density of pairs of atoms, when identifying a reduction in electronic density. The Calculation of percentage reduction is performed using Eq.\u0026nbsp;(\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e) given below:\u0026nbsp;\u003c/p\u003e\n \u003ctable border=\"1\" id=\"Tab1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eComparison of bond length (L (\u0026Aring;); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆\u003cem\u003e\u0026rho;\u003c/em\u003e) of benzene molecule neutral and dicationic; and percentage reduction (PR) in the electronic density\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eExp.[\u003cspan class=\"CitationRef\"\u003e38\u003c/span\u003e]\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" colspan=\"4\"\u003e\n \u003cp\u003eNeutral\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" colspan=\"4\"\u003e\n \u003cp\u003eDicationic\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBond\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e∆\u003cem\u003eBO\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e∆\u003cem\u003e\u0026rho;\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePR%\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003er(C1-C2)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.3971\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.399\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.456\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.304\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e-0.740\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.464\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.813\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.280\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e-0.688\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.643\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.025\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e-7.895\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003er(C2-C3)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.3971\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.399\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.455\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.305\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.740\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.397\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.209\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.301\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.725\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.246\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.003\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-1.311\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003er(C3-C4)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.3971\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.399\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.457\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.304\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.740\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.397\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.209\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.301\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.725\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.248\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.003\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.987\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003er(C4-C5)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.3971\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.399\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.456\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.304\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e-0.740\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e1.464\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.813\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.280\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e-0.688\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.643\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e0.025\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e-7.895\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003er(C5-C6)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.3971\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.399\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.455\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.305\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.740\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.397\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.209\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.301\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.725\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.246\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.003\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-1.311\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003er(C6-C1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.3971\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.399\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.457\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.304\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.740\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.397\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.209\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.301\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.725\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.248\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.003\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-0.987\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCCC (\u003cem\u003eo\u003c/em\u003e)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" colspan=\"4\"\u003e\n \u003cp\u003e119.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\" colspan=\"4\"\u003e\n \u003cp\u003e123.2-107.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003cp\u003e\u003c/p\u003e\n \u003cdiv class=\"Equation\" id=\"Equ1\"\u003e\n \u003cdiv class=\"mathdisplay\" id=\"FileID_Equ1\" name=\"EquationSource\"\u003e$$PR\\text{%}=\\left(\\frac{{\\rho }_{Dication}}{{\\rho }_{Neutral}}-1\\right)\\times 100$$\u003c/div\u003e\u003cdiv class=\"EquationNumber\"\u003e1\u003c/div\u003e\u003c/div\u003e\u003cp\u003eTable \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e shows the pairs of atoms r(C1-C2) and r(C4-C5) of the BZ\u003csup\u003e2+\u003c/sup\u003e molecule, which have lower bond order, lower electronic density, and also a percentage of reduction of -7.895%, concerning the neutral molecule. In addition, it is possible to form two types of fragments C\u003csub\u003e2\u003c/sub\u003eH\u003csub\u003e2\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e, and C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e of mass-to-charge ratio m/e\u0026thinsp;=\u0026thinsp;26, and m/e\u0026thinsp;=\u0026thinsp;39, respectively. They are potentially favorable fragments, and sufficient to maintain consistency with the experimental results of mass spectrometry of benzene molecule [\u003cspan class=\"CitationRef\"\u003e39\u003c/span\u003e\u0026ndash;\u003cspan class=\"CitationRef\"\u003e43\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eTable \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e shows r(C2-C3), r(C4-C5), r(C5-C6), and r(C7-C2) bond lengths of the ANI and ANI\u003csup\u003e2+\u003c/sup\u003e molecules, which have lower bond order and lower electronic. However, r(C2-C3) and r(C7-C2) bond lengths have a significant percentage of reduction with values around \u0026minus;\u0026thinsp;11.3%. This percentage is a strong indication of the break bond position with the possibility of formation of the C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e and C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e fragments of the mass-to-charge ratio of m/e\u0026thinsp;=\u0026thinsp;65 and m/e\u0026thinsp;=\u0026thinsp;66, respectively. The fragments show consistency with the result found in the literature [\u003cspan class=\"CitationRef\"\u003e44\u003c/span\u003e\u0026ndash;\u003cspan class=\"CitationRef\"\u003e46\u003c/span\u003e].\u0026nbsp;\u003c/p\u003e\u003ctable border=\"1\" id=\"Tab2\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eComparison of bond length (L (\u0026Aring;); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆\u003cem\u003e\u0026rho;\u003c/em\u003e) of aniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eExp.[\u003cspan class=\"CitationRef\"\u003e39\u003c/span\u003e]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003eNeutral\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"5\"\u003e\u003cp\u003eDicationic\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003eBond\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆BO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆\u0026rho;\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003ePR%\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003er(N1-C2)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.402\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.400\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.962\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e0.296\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.908\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.295\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.542\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e0.360\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.703\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.580\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.064\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e21.622\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003er(C2-C3)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.397\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.407\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.931\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.301\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.728\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.485\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.630\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.267\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.637\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.301\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.035\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-11.296\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003er(C3-C4)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.394\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.396\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.434\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e0.305\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.736\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.361\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.955\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e0.329\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.849\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.521\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.024\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e7.869\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003er(C4-C5)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.396\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.399\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.439\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.304\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.736\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.441\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.021\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.288\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.707\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.418\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.016\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-5.263\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003er(C5-C6)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.399\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.439\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.304\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.736\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.441\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.021\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.288\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.707\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.418\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.016\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-5.263\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003er(C6-C7)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.396\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.434\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e0.305\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.736\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.361\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.955\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e0.329\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.849\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.521\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.024\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e7.869\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003er(C7-C2)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.407\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.931\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.301\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.728\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.485\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.630\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e0.267\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.637\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.301\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.035\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-11.296\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003eHNH (\u0026ordm;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e113.10\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003e111.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"5\"\u003e\u003cp\u003e115.5\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003eHNC (\u0026ordm;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e115.94\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003e115.5\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"5\"\u003e\u003cp\u003e122.2\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003cp\u003e\u003c/p\u003e\u003cbr\u003e\u0026nbsp;\u003ctable\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"17\"\u003e\u003cp\u003e\u003cstrong\u003eTable\u0026nbsp;3.\u003c/strong\u003e Comparison of bond length (L (\u0026Aring;); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆\u003cem\u003eBO\u003c/em\u003e); electron density difference (∆\u003cem\u003e\u0026rho;\u003c/em\u003e) of o-nitroaniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density.\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003eExp[\u003cspan class=\"CitationRef\"\u003e40\u003c/span\u003e],[\u003cspan class=\"CitationRef\"\u003e41\u003c/span\u003e]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"5\"\u003e\u003cp\u003eNeutral\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003eDicationic\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBond\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆BO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆\u0026rho;\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003ePR%\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(N1-C2)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.455\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.358\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.148\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.322\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-1.056\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.290\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.457\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.368\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.795\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.309\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.047\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e14.286\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C2-C3)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.402\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.426\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.102\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.291\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.686\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.491\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.600\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.265\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.620\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.960\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.027\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-8.935\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(C3-C4)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.387\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.408\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.90\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.300\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.723\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.355\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.733\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.333\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.872\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.643\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.033\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e11.000\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C4-C5)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.374\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.383\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.961\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.312\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.768\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.449\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.305\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.283\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.687\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.656\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.029\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-9.295\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(C5-C6)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.380\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.409\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.649\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.299\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.723\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.428\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.302\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.294\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.730\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.347\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.005\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-1.672\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(C6-C7)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.383\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.383\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.505\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.313\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.769\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.366\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.756\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.326\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.842\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.251\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.013\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e4.153\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C7-C2)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.379\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.421\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.477\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.294\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.706\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.488\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.366\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.266\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.631\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.111\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.029\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-9.524\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C3-N9)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.451\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.450\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.871\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.266\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.671\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e1.507\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.676\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.254\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e\u003cstrong\u003e-0.570\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.195\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.012\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-4.511\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(N9-O8)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.217\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.245\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.860\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.494\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-1.038\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.235\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.949\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.528\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-1.151\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.890\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.034\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e6.883\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(N9-O10)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.226\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.230\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.914\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.476\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.976\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e1.203\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.102\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.488\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-0.995\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.188\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.011\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e2.521\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eHNH (\u0026ordm;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"5\"\u003e\u003cp\u003e121.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003e121.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eHNO (\u0026ordm;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"2\"\u003e\u003cp\u003e124.7\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"5\"\u003e\u003cp\u003e122.4\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003e127.4\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003cbr\u003e\u003cp\u003eTable\u0026nbsp;3 shows r(C2-C3) and r(C4-C5) bond lengths with lower bond order, and r(C2-C3), r(C4-C5), and r(C7-C2) bond lengths with lower electronic density for the neutral and dicationic molecules of oNA. However, the results show a percentage of reduction of -8.935% for r(C2-C3), -9.295% for r(C4-C5), and \u0026minus;\u0026thinsp;9.524% for r(C7-C2). There is possibility of formation of C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e and C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e fragments of mass-to-charge ratio of m/e\u0026thinsp;=\u0026thinsp;92 and m/e\u0026thinsp;=\u0026thinsp;66, respectively. The fragments show consistency with the result found in the literature [\u003cspan class=\"CitationRef\"\u003e23\u003c/span\u003e],[\u003cspan class=\"CitationRef\"\u003e24\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eTable \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e shows r(C2-C3), r(C5-C6), and r(C7-C2) bond lengths with lower bond order, and r(C2-C3) and r(C7-C2) bond lengths with lower electronic density for the neutral and dicationic molecules of mNA2+. There are two bond lengths with a significant percentage of reduction of -9.603% for r(C2-C3) and \u0026minus;\u0026thinsp;11.296% for r(C7-C2). There is possibility of formation of C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e, C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e, and C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e fragments of mass-to-charge ratio of m/e\u0026thinsp;=\u0026thinsp;65, m/e\u0026thinsp;=\u0026thinsp;80 and m/e\u0026thinsp;=\u0026thinsp;92, respectively. The fragments show consistency with the result found in the literature [\u003cspan class=\"CitationRef\"\u003e24\u003c/span\u003e],[\u003cspan class=\"CitationRef\"\u003e25\u003c/span\u003e].\u0026nbsp;\u003c/p\u003e\u003ctable border=\"1\" id=\"Tab3\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 4\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eComparison of bond length (L (\u0026Aring;); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆\u003cem\u003e\u0026rho;\u003c/em\u003e) of m-nitroaniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eExp.[\u003cspan class=\"CitationRef\"\u003e2\u003c/span\u003e]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003eNeutral\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003eDicationic\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBond\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆BO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆\u0026rho;\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003ePR%\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(N1-C2)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.380\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.392\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.949\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.302\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.942\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.301\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.465\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.357\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.773\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.516\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.055\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e18.212\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C2-C3)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.405\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.329\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.302\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.731\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.468\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.828\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.273\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.651\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.501\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.029\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-9.603\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(C3-C4)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.393\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.551\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.308\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.752\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.356\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.218\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.331\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.850\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.667\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.024\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e7.468\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C4-C5)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.395\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.526\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.307\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.755\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.441\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.678\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.290\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.714\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.152\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.018\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-5.538\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C5-C6)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.397\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.792\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.304\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.737\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.430\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.288\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.292\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.721\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.504\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.012\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-3.947\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(C6-C7)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.395\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.562\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.306\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.742\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.366\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.848\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.325\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.837\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.286\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.020\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e6.209\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003er(C7-C2)\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.410\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.109\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.301\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.728\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.486\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.648\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.267\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.635\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.461\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.034\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-11.296\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(C4-N9)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.457\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.479\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.657\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.254\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.623\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.483\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.703\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.265\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.654\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.460\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.011\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e4.331\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(N9-O8)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.222\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.230\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.869\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.496\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-1.051\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.203\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.125\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.490\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-1.019\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.256\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.006\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-1.210\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(N9-O10)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.221\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.228\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.804\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.495\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-1.045\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.235\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.027\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.526\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-1.131\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.223\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.031\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e6.263\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eHNH (o)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e114.6\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e113.0\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e115.5\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eHNO (o)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e122.8\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e124.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e128.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003cp\u003e\u003c/p\u003e\u003cp\u003e\u003cbr\u003e\u003c/p\u003e\u003cp\u003eTable \u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003e shows r(C2-C3), r(C3-C4), r(C6-C7), r(C7-C2), and r(C5-N9 ) bond lengths with lower bond order, and r(C2-C3), r(C4-C5), r(C5-C6), r(C7-C2) and r(N9-O10) bond lengths with lower electronic density for the neutral and dicationic molecules of pNA\u003csup\u003e2+\u003c/sup\u003e. There are five bond lengths with a significant percentage of reduction of -9.030% for r(C2-C3), -7.213% for r(C4-C5), -7.213% for r(C5-C6), -9.030% for r(C7-C2), and 4.684% for r(N9-O10). There is possibility of formation of C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e, C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e+, and C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eNO\u003csup\u003e+\u003c/sup\u003e fragments with mass-to-charge ratio of m/e\u0026thinsp;=\u0026thinsp;80, m/e\u0026thinsp;=\u0026thinsp;92, and m/e\u0026thinsp;=\u0026thinsp;107, respectively. The fragments show consistency with the result found in the literature [\u003cspan class=\"CitationRef\"\u003e24\u003c/span\u003e],[\u003cspan class=\"CitationRef\"\u003e26\u003c/span\u003e],[\u003cspan class=\"CitationRef\"\u003e27\u003c/span\u003e].\u0026nbsp;\u003c/p\u003e\u003ctable border=\"1\" id=\"Tab4\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 5\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eComparison of bond length (L (\u0026Aring;); bond order (BO); QTAIM properties at the bond critical points (BCP); bond order difference (∆BO); electron density difference (∆\u003cem\u003e\u0026rho;\u003c/em\u003e) of p-nitroaniline molecule neutral and dicationic; and percentage reduction (PR) in the electronic density\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eExp.[\u003cspan class=\"CitationRef\"\u003e2\u003c/span\u003e]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003eNeutral\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003eDicationic\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBond\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eL (\u0026Aring;)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎03)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho\\)\u003c/span\u003e\u003c/span\u003e(1/𝑎05)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆BO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e∆\u0026rho;\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003ePR%\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(N1-C2)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.355\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.380\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.064\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.307\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.978\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.301\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.458\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.357\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.795\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.394\u003c/p\u003e\u003c/td\u003e\u003ctd 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align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.305\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.746\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.445\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.908\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.283\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.686\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.426\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.022\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-7.213\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003er(C6-C7)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.388\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e2.204\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.309\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.751\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.356\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.977\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.330\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-0.842\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.227\u003c/p\u003e\u003c/td\u003e\u003ctd 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align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.235\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.233\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.861\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.491\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-1.027\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.254\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e1.056\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.468\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.928\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-0.195\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e0.023\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003e-4.684\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eHNH (o)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e120.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e114.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e115.6\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eHNO (o)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e122\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e123.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\" colspan=\"4\"\u003e\u003cp\u003e132.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003cp\u003e\u003c/p\u003e\u003cp\u003e\u003cbr\u003e\u003c/p\u003e\u003cp\u003eThere was a significant increase in the bond order in the dicationic states in relation to the isomeric positions of the r(N1-C2) bond length, following the order: oNA\u003csup\u003e2+\u003c/sup\u003e (26.92%)\u0026thinsp;\u0026lt;\u0026thinsp;pNA\u003csup\u003e2+\u003c/sup\u003e (45.8%)\u0026thinsp;\u0026lt;\u0026thinsp;mNA\u003csup\u003e2+\u003c/sup\u003e (54.4%). In relation to the isomeric positions of the r(CX-N9; X is the atom number\u0026thinsp;=\u0026thinsp;3, 4 and 5) bond length, there was a change in the bond length following the order: mNA\u003csup\u003e2+\u003c/sup\u003e (-39.7%)\u0026thinsp;\u0026gt;\u0026thinsp;oNA\u003csup\u003e2+\u003c/sup\u003e (-22.4%). However, there is an increase in the bond order of pNA\u003csup\u003e2+\u003c/sup\u003e (7%) due to charge relocation which can be favorable to the electron transfer by the -NO\u003csub\u003e2\u003c/sub\u003e group in the pNA\u003csup\u003e2+\u003c/sup\u003e. Therefore, the best relocation of charge is an indication of an increase in the bond order[\u003cspan class=\"CitationRef\"\u003e28\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eThe electron transfer possibility an analysis from this first analysis based on electrostatic potential maps can relate the changes in the bond order, the electronic density, and positive/negative regions. The electrostatic potential map (PES) [\u003cspan class=\"CitationRef\"\u003e29\u003c/span\u003e] is a tool used to determine the reactive regions of nucleophilic and electrophilic attacks in a molecular system.\u003c/p\u003e\u003cp\u003eFigure \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e shows the map of the potential energy surface generated by the electron isodensity surface of 0.02/a.u3 for each point on the map for the molecules of BZ, ANI, oNA, mNA, and pNA. Thereby, the increase in bond orders of the -NH2 group, and the reduction of bond orders for the group -NO\u003csup\u003e2\u003c/sup\u003e can be analyzed with help of electrostatic potential maps from the electrostatic interactions between species doubly ionized. These areas of electrostatic potentials can be displayed as isocontour surfaces (maps of electron density).\u003c/p\u003e\u003cp\u003eThe electrostatic potential maps of neutral and dicationic molecules indicate a lower charge concentration in all dications, mainly in the dark blue regions, justified by the decrease in the -NH\u003csub\u003e2\u003c/sub\u003e group bond order. The regions of positive electrostatic potential are concentrated mainly on the nitrogen atoms of the amine group and also on the hydrogen atoms. The dark blue and light blue areas represent a positive potential of atoms -H bond to the nitrogen and ring carbon atoms. However, due to the influence of the -NO\u003csub\u003e2\u003c/sub\u003e group, which determines the character of a negative charge, this potential map is changed and these changes are represented in the regions in red, negative potential. The loss of two electrons in the (f), (g), (h), (i), and (j) monomers; leaving the peripheral regions to the center of the ring more positive (surface observed in dark blue and light blue) toward the center of the ring for bonds with lower bond order. The electron-donating groups, such as the -NH\u003csub\u003e2\u003c/sub\u003e, increase the electron density in the positions \u003cem\u003eortho-\u003c/em\u003e, \u003cem\u003emeta-\u003c/em\u003e, and \u003cem\u003epara-\u003c/em\u003e in an aromatic of the Kekul\u0026eacute;\u0026apos;s circuits type[\u003cspan class=\"CitationRef\"\u003e30\u003c/span\u003e] (electron-withdrawing groups).\u003c/p\u003e\u003cp\u003eWiberg\u0026apos;s binding indices and Bader\u0026apos;s topological analysis satisfactorily describe the weaker connections of molecular systems in the studies. In the comparison of the results found by both theories, it was necessary to define the connections with lower charge concentrations, with greater possibilities of breaking chemical bonds. In order to do this, electronic density maps and the Laplacian electronic density (topological analysis), show curves, and regions of higher concentrations of charge on the bonds in the layer of valence [\u003cspan class=\"CitationRef\"\u003e31\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eThe electronic densities are located in pairs of atoms showing higher and lower concentrations of charge, especially in the regions probable to break bonds at the dications. The pairs of atoms that have connected regions have higher concentrations of load on the bonds and are less likely to break the bond in these regions [\u003cspan class=\"CitationRef\"\u003e32\u003c/span\u003e].\u003c/p\u003e\u003cp\u003eFrom Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e, it is possible to observe the different concentrations of charge. The BZ molecule (a) shows concentrations of uniform charges throughout its structure, but the BZ\u003csup\u003e2+\u003c/sup\u003e molecule (C) shows a low concentration of charge (or lower electronic density) in the r(C1-C2), and r(C4-C5) bond lengths. The ANI molecule (b) removes the uniformity of density in the aromatic ring due to group -NH\u003csub\u003e2\u003c/sub\u003e. The change in the electronic density of ANI\u003csup\u003e2+\u003c/sup\u003e molecule (d) shows a difference between the electronic densities in the r(C2-C3), r(C4-C5), r(C5-C6), and r(C7-C2) bond lengths.\u003c/p\u003e\u003cp\u003eAt the top of Fig. \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e, the neutral states of the oNA (a), mNA (b), and pNA (c) molecules are shown. The oNA (a) molecule presents intramolecular interaction between the oxygen from the nitro group and the hydrogen from the amino group, which indicates that the nuclei support all concentrations of charge (\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({\\nabla }^{2}\\rho \\left(r\\right)\\)\u003c/span\u003e\u003c/span\u003e \u0026gt; 0). Whilst, oNA\u003csup\u003e2+\u003c/sup\u003e molecule (d) shows a significant increase in the electronic density in the region of interaction H\u0026sdot;\u0026sdot;\u0026sdot;O(8)-, and a lower electronic density in the r(C2-C3), r(C4-C5), r(C7-C2), and r(C3-N9) bond lengths. The mNA\u003csup\u003e2+\u003c/sup\u003e (e) and pNA\u003csup\u003e2+\u003c/sup\u003e (f) molecules show the lower concentrations of charge in r(C2-C3), r(C4-C5), r(C5-C6), r(C7-C2), and r(N9-O8) bond lengths in relation to the neutral molecule. Therefore, with the relaxation of the system, the charge distribution is altered, thus leaving some pairs of atoms weaker than the others and this can be seen in the electronic density maps, represented graphically for neutral and doubly ionized species.\u003c/p\u003e\u003cp\u003eEven though, the possibility to find a route of fragmentation by the reduction of the electronic densities (using Bader\u0026rsquo;s protocol) of chemical bonds in molecule dicationics, not all pairs of atoms involved in this analysis converge to the result of the analysis in terms of the bond orders. Therefore, the use of both methods to estimate the chemical bonds are necessary.\u003c/p\u003e\u003c/div\u003e\u003cdiv class=\"Section2\" id=\"Sec5\"\u003e\u003ch2\u003e3.2. Thermodynamic properties\u003c/h2\u003e\u003cp\u003eIn addition, we approach the thermodynamic properties of each neutral and doubly ionized molecular structure and mix it with other results found in the literature, to assemble Table \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003e, which was very useful in the construction of Table \u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003e, where the results of the enthalpy calculations are found. formation at temperatures of 0K and 298K, and Gibbs free energy.\u0026nbsp;\u003c/p\u003e\u003cbr\u003e\u003ctable border=\"1\" id=\"Tab5\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 6\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eStandard enthalpy of formation of neutral elements (\u003cspan style='color: rgb(0, 0, 0); font-family: \"Times New Roman\"; font-size: medium; font-style: normal; font-variant-ligatures: normal; font-variant-caps: normal; font-weight: 700; letter-spacing: normal; orphans: 2; text-align: -webkit-left; text-indent: 0px; text-transform: none; white-space: normal; widows: 2; word-spacing: 0px; -webkit-text-stroke-width: 0px; text-decoration-thickness: initial; text-decoration-style: initial; text-decoration-color: initial; display: inline !important; float: none;'\u003e\u0026Delta;\u003c/span\u003eHo), Standard enthalpy of formation at 0K, and entropy at 298K of the cationic elements (\u003cspan style='color: rgb(0, 0, 0); font-family: \"Times New Roman\"; font-size: medium; font-style: normal; font-variant-ligatures: normal; font-variant-caps: normal; font-weight: 700; letter-spacing: normal; orphans: 2; text-align: -webkit-left; text-indent: 0px; text-transform: none; white-space: normal; widows: 2; word-spacing: 0px; -webkit-text-stroke-width: 0px; text-decoration-thickness: initial; text-decoration-style: initial; text-decoration-color: initial; display: inline !important; float: none;'\u003e\u0026Delta;\u003c/span\u003efHo in kcal.mol-1 and \u0026Delta;So in kcal.mol-1K-1, respectively)\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eNeutral\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u0026Delta;Ho [a]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eion\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u0026Delta;fHo (X,0K)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u0026Delta;So(X,298K)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eH\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.01\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eH+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e365.20[b]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e26.012\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eC\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.25\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eC+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e429.60[c]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e34.773\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eN\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.04\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eN+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e447.60[d]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e33.856\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eO\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.04\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eO+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e373.04[e]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e35.629\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"7\"\u003e\u003cp\u003e[a] ref.[\u003cspan class=\"CitationRef\"\u003e33\u003c/span\u003e]; [b] Ref.[\u003cspan class=\"CitationRef\"\u003e42\u003c/span\u003e]; [c] Ref.[\u003cspan class=\"CitationRef\"\u003e34\u003c/span\u003e]; [d] Ref.[\u003cspan class=\"CitationRef\"\u003e43\u003c/span\u003e]; [e] Ref.[\u003cspan class=\"CitationRef\"\u003e44\u003c/span\u003e]\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003cp\u003e\u003c/p\u003e\u003cdiv class=\"gridtable\"\u003e\u003cdiv align=\"left\" class=\"colspec\"\u003e\u003cbr\u003e\u003c/div\u003e\u0026nbsp;\u003ctable border=\"1\" id=\"Tab6\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 7\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eMolecular ions, doubly ionized, atomic mass unit (amu), fragmentation channels, and the enthalpy of formation (0K and 298K) and their Gibbs free energies (kcal.mol\u0026thinsp;\u0026minus;\u0026thinsp;1).\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e \u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\"\u003e\u003cp\u003eNeutral\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\"\u003e\u003cp\u003emolecule\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\"\u003e\u003cp\u003eMass (amu)\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\"\u003e\u003cp\u003e∆\u003cem\u003eHo(0k)\u003c/em\u003e\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\"\u003e\u003cp\u003e∆\u003cem\u003eHo(298k)\u003c/em\u003e\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\"\u003e\u003cp\u003e∆\u003cem\u003eGo(298k)\u003c/em\u003e\u003c/p\u003e\u003c/th\u003e\u003c/tr\u003e\u003c/thead\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBZ\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eC6H62+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e78\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e559.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e556.1\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e645.0\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eANI\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eC6H5NH2+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e93\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e423.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e418.6\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e592.4\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eONA\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eC6H6N2O2\u0026thinsp;+\u0026thinsp;2\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e138\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e181.7\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e175.8\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e636.9\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eMNA\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eC6H6N2O2\u0026thinsp;+\u0026thinsp;2\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e138\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e175.0\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e169.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e635.0\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003ePNA\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eC6H6N2O2\u0026thinsp;+\u0026thinsp;2\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e138\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e168.0\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e162.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e630.3\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003c/div\u003e\u003cp\u003e\u003cbr\u003e\u003c/p\u003e\u003cp\u003eIn Table \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003e we present the ions: hydrogen (H\u003csup\u003e+\u003c/sup\u003e), carbon (C\u003csup\u003e+\u003c/sup\u003e), nitrogen (N\u003csup\u003e+\u003c/sup\u003e), and oxygen (O\u003csup\u003e+\u003c/sup\u003e), with the combination of thermodynamic properties of enthalpies formation of neutral elements (H\u003csub\u003e298K\u003c/sub\u003e-H\u003csub\u003e0K\u003c/sub\u003e) with the enthalpies of formation of the cationic atoms and between the calculated entropies of each ion (\u003cem\u003eS\u003c/em\u003e\u003csup\u003e\u003cem\u003eo\u003c/em\u003e\u003c/sup\u003e\u003csub\u003e\u003cem\u003e298K\u003c/em\u003e\u003c/sub\u003e), seeking a better approximation of the energy properties of the molecular ions listed in Table \u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003e. But, to generate each value enthalpy of formation (\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\varDelta {H}_{0K}^{o}\\)\u003c/span\u003e\u003c/span\u003e and \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\varDelta {H}_{298K}^{o}\\)\u003c/span\u003e\u003c/span\u003e) and Gibbs free energy (\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\varDelta {G}_{298K}^{o}\\)\u003c/span\u003e\u003c/span\u003e). The Eq.\u0026nbsp;(\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e) represents the enthalpy of formation in 0K, where \u003cem\u003ex\u003c/em\u003e is the number of atoms of X that represents each element of a molecule M, and \u0026sum;D\u003csub\u003eo\u003c/sub\u003e(M) represents the atomization energy of the molecule (M).\u003c/p\u003e\u003cdiv class=\"Equation\" id=\"Equ2\"\u003e\u003cdiv class=\"mathdisplay\" id=\"FileID_Equ2\" name=\"EquationSource\"\u003e$${\\varDelta }_{f}{H}_{0K}^{o}=\\sum _{atoms}x{\\varDelta }_{f}{H}_{(X;0K)}^{o}-\\sum _{atoms}{D}_{o}\\left(M\\right)$$\u003c/div\u003e\u003cdiv class=\"EquationNumber\"\u003e2\u003c/div\u003e\u003c/div\u003e\u003cp\u003eEquation (\u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e) represents the enthalpy of formation in 298K, where\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({H}_{M}^{o}\\left(298K\\right)-{H}_{M}^{o} \\left(0K\\right)\\)\u003c/span\u003e\u003c/span\u003e represents the correction of the enthalpy for the molecule M, and\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({H}_{X}^{o}\\left(298K\\right)-{H}_{X}^{o}\\left(0K\\right)\\)\u003c/span\u003e\u003c/span\u003e is the correction of the enthalpy of atomic elements X.\u003c/p\u003e\u003cdiv class=\"Equation\" id=\"Equa\"\u003e\u003cdiv class=\"mathdisplay\" id=\"FileID_Equa\" name=\"EquationSource\"\u003e$${\\varDelta H}_{298 K}^{o}={\\varDelta H}_{0 K}^{o}+\\left[{\\varDelta H}_{M}^{o} \\left(298K\\right)-{\\varDelta H}_{M}^{o} \\left(0K\\right)\\right]$$\u003c/div\u003e\u003c/div\u003e\u003cdiv class=\"Equation\" id=\"Equ3\"\u003e\u003cdiv class=\"mathdisplay\" id=\"FileID_Equ3\" name=\"EquationSource\"\u003e$$-\\sum x\\left[{\\varDelta H}_{M}^{o} \\right(298K)-{\\varDelta H}_{M}^{o} (0K\\left)\\right]$$\u003c/div\u003e\u003cdiv class=\"EquationNumber\"\u003e3\u003c/div\u003e\u003c/div\u003e\u003cp\u003eThe Eq.\u0026nbsp;(\u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e) represents the Gibbs free energy in 298K, where\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({S}_{(M, 298K)}^{o}\\)\u003c/span\u003e\u003c/span\u003e and\u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\({S}_{(X, 298K)}^{o}\\)\u003c/span\u003e\u003c/span\u003e represent the enthalpy of reaction of the molecule M, the entropy of atoms.\u003c/p\u003e\u003cdiv class=\"Equation\" id=\"Equ4\"\u003e\u003cdiv class=\"mathdisplay\" id=\"FileID_Equ4\" name=\"EquationSource\"\u003e$$\\varDelta {G}_{298K}{H}_{0K}^{o}={\\varDelta }_{r}{H}_{\\left(298K\\right)}^{o}-298.15({S}_{(M,298K)}^{o}-\\sum {S}_{(x,298K)}^{o})$$\u003c/div\u003e\u003cdiv class=\"EquationNumber\"\u003e4\u003c/div\u003e\u003c/div\u003e\u003cp\u003eThe equations (\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e), (\u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e), and (4) were used to calculate the assemble in Table \u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003e, based on the References [\u003cspan class=\"CitationRef\"\u003e33\u003c/span\u003e], [\u003cspan class=\"CitationRef\"\u003e34\u003c/span\u003e] and [\u003cspan class=\"CitationRef\"\u003e35\u003c/span\u003e]. We present in Table \u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003e the doubly ionized molecular ions of benzene, aniline, and nitroaniline (ortho, meta, and para), accompanied by their atomic masses of its enthalpies of formation in 0K, and 298K; and their Gibbs free energies.\u003c/p\u003e\u003cp\u003eFor positive energies, we have a non-spontaneous process, due to the removal of two electrons of the system requiring a large amount of energy (Ionization Potential - \u003cem\u003eIP\u003c/em\u003e) for which the electrons are ejected out of the layer of the valence of the molecule. However, we found a paper that refers to the heat of formation of benzene doubly ionized experimental value of 26.0 eV\u0026thinsp;=\u0026thinsp;599.57 kcal.mol-1 [\u003cspan class=\"CitationRef\"\u003e36\u003c/span\u003e]. From the values of ground state energy of the systems, it was possible to calculate the \u003cem\u003eIP\u003c/em\u003e of the structures using Eq. (5) [\u003cspan class=\"CitationRef\"\u003e37\u003c/span\u003e].\u003c/p\u003e\u003cp\u003e\u003cem\u003eIP\u003c/em\u003e\u0026thinsp;=\u0026thinsp;\u003cem\u003eE\u003c/em\u003e\u003csub\u003eN\u0026minus;1\u003c/sub\u003e - \u003cem\u003eE\u003c/em\u003e\u003csub\u003eN\u003c/sub\u003e (5)\u003c/p\u003e\u003cp\u003eWhere \u003cem\u003eE\u003c/em\u003e\u003csub\u003e(N\u0026minus;1)\u003c/sub\u003e and \u003cem\u003eE\u003c/em\u003e\u003csub\u003eN\u003c/sub\u003e are the total energies of the (N-1) and N electron system, respectively. Table \u003cspan class=\"InternalRef\"\u003e8\u003c/span\u003e shows the values of electronic energy (E\u003csub\u003e0\u003c/sub\u003e), dipole moment (\u003cem\u003e\u0026micro;\u003c/em\u003e), and ionization potential (\u003cem\u003eIP\u003c/em\u003e), of neutral molecules, and dicationics; and compare them with some experimental results found in the literature. The results show a good approximation of our theoretical calculations with experimental results, revealing that the neutral molecules have theoretical results of the dipole moment of ionization potential, and are very close to the experimental results.\u0026nbsp;\u003c/p\u003e\u003ctable border=\"1\" id=\"Tab7\"\u003e\u003ccaption language=\"En\"\u003e\u003cdiv class=\"CaptionNumber\"\u003eTable 8\u003c/div\u003e\u003cdiv class=\"CaptionContent\"\u003e\u003cp\u003eDipole moments (\u0026micro;) and ionization potential (IP) for neutral and dicationic chemical species at the UB3LYP/aug-cc-pVDZ calculation level, and experimental values found in the literature.\u003c/p\u003e\u003c/div\u003e\u003c/caption\u003e\u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\"\u003e\u003cp\u003eMolecules\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colspan=\"3\"\u003e\u003cp\u003eTheoretical\u003c/p\u003e\u003c/th\u003e\u003cth align=\"left\" colspan=\"2\"\u003e\u003cp\u003eExp.\u003c/p\u003e\u003c/th\u003e\u003c/tr\u003e\u003c/thead\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eE\u003cem\u003eT\u003c/em\u003e (a.u)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cem\u003e\u0026micro;\u003c/em\u003e[D]*\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eIP (eV)\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cem\u003e\u0026micro;\u003c/em\u003e[D]*\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eIP (eV)\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003eNeutral\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBZ\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-232.27460349\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.0\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e9.1\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.0[a]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e9.24[c]\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eANI\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-287.64377206\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.6\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e7.5\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e1.5[b]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e7.72[d]\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eONA\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-492.18807246\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e4.9\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e8.2\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e4.3[b]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e8.43[e]\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eMNA\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-492.18374531\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e5.8\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e8.2\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e4.9[b]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e8.60[f]\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003ePNA\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-492.18774648\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e7.4\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e8.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e6.2[b]\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e8.43[f]\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e\u003cstrong\u003eDicationic\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eBZ2+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-231.37763151\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e0.0\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e21.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eANI2+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-286.86572780\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e2.8\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e20.3\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eONA2+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-491.36806291\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e10.1\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e19.8\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003eMNA2+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-491.36709206\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e12.5\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e19.4\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\"\u003e\u003cp\u003ePNA2+\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-491.37881464\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e10.8\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e20.2\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003ctd align=\"left\"\u003e\u003cp\u003e-\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003e[D]* = 1 Debye\u0026thinsp;=\u0026thinsp;3.33564 x 10\u0026ndash;30 C.m\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colspan=\"6\"\u003e\u003cp\u003e[a] ref.[\u003cspan class=\"CitationRef\"\u003e45\u003c/span\u003e]; [b] Ref.[\u003cspan class=\"CitationRef\"\u003e46\u003c/span\u003e]; [c] Ref.[\u003cspan class=\"CitationRef\"\u003e47\u003c/span\u003e]; [d] Ref.[\u003cspan class=\"CitationRef\"\u003e48\u003c/span\u003e]; [e] Ref.[\u003cspan class=\"CitationRef\"\u003e49\u003c/span\u003e]; [f] Ref.[\u003cspan class=\"CitationRef\"\u003e50\u003c/span\u003e].\u003c/p\u003e\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003c/div\u003e"},{"header":"Conclusion","content":"\u003cp\u003eThe investigation of a theoretical molecular fragmentation route may be possible through the application of two methods: Wiberg's bond indexes and Bader\u0026rsquo;s topological analysis (QTAIM). In addition, the electrostatic potential maps, indicate the most positive areas of the molecules that coincide with the reduction in electronic densities.\u003c/p\u003e \u003cp\u003eAfter careful analysis of the obtained results, such as bond length, bond order, and electronic density, we verified that these methodologies take to the same conclusion as our previous analysis for the BZ\u003csup\u003e2+\u003c/sup\u003e case, which has two sigma bonds, with smaller bond orders, and more positive areas in the proximities of the ligands of smaller electronic densities, and the possibility to form fragments of the type C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e, and C\u003csub\u003e2\u003c/sub\u003eH\u003csub\u003e2\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e. The ANI\u003csup\u003e2+\u003c/sup\u003e possesses four ligands with smaller bond orders, more positive areas in the proximities of the ligands with a percentage reduction in the electronic densities, and the possibility to form fragments of the type C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e, and C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003eThe oNA\u003csup\u003e2+\u003c/sup\u003e presents five ligands with smaller bond orders, more positive areas in the proximities of the ligands of percentage reduction in the electronic densities, and the possibility of forming fragments of the type C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e, and C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003eThe mNA\u003csup\u003e2+\u003c/sup\u003e has three ligands with lower binding orders and more positive areas in the vicinity of the ligands, and present percentage reduction in the electronic densities with the possibility to form fragments of the type C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003e\u003csup\u003e+\u003c/sup\u003e, C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e, and C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003eThe pNA2\u0026thinsp;+\u0026thinsp;presents the ligands r(C4-C5) and r(C5-C6) as being the main ligands involved in the formation of the fragments C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003e+, C\u003csub\u003e5\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+,\u003c/sup\u003e and C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eN\u003csup\u003e+\u003c/sup\u003e, but, it has more than four ligands with smaller orders and more positive areas in the vicinity of the ligands, a percentage reduction in electronic densities.\u003c/p\u003e \u003cp\u003eWe verified that the process of charge transfer and electronic distribution in the nitroanilines occurs in the area of the group -NO\u003csub\u003e2\u003c/sub\u003e. The donor or acceptor of the electrons groups changes the percentage of the density, and the bond order, as in the case of the pairs of atoms at isomeric positions.\u003c/p\u003e \u003cp\u003eGenerating like this, π bonds of the low bond index, and electronic delocalization in the ring of the neutral system, as seen previously in Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e of the electrostatic maps of surfaces of potential energy. Still, in the result of our analyses of QTAIM, it was revealed that the largest densities of charges are located in the group -NH\u003csub\u003e2\u003c/sub\u003e of the dications, and the smallest densities of charges in the groups C-NH\u003csub\u003e2\u003c/sub\u003e, and -NO\u003csub\u003e2\u003c/sub\u003e, start a possible process of molecular fragmentation in the dicationic nitroanilines. Thus, we conclude that both methodologies applied in the investigation of a fragmentation route lead to the indication of weakened bonds due to the removal of two electrons from the system, it may be due to the reduction of the order of the bonds or by the percentage reduction in the electronic density.\u003c/p\u003e "},{"header":"Abbreviations","content":"\u003cp\u003eoNA \u0026nbsp; \u0026nbsp;ortho- Nitroanilines\u003c/p\u003e\n\u003cp\u003emNA \u0026nbsp; meta- Nitroanilines\u003c/p\u003e\n\u003cp\u003epNA \u0026nbsp; para-Nitroanilines\u003c/p\u003e\n\u003cp\u003eBZ \u0026nbsp; \u0026nbsp; Benzene\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eANI \u0026nbsp; Aniline\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eNA \u0026nbsp; \u0026nbsp;Nitroanilines\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eDeclaration of Competing Interest\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare that there is no conflict of interests regarding the publication of this research paper.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthorship contribution statement\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eMs. Carlos Xavier de Oliveira\u003c/strong\u003e: Conceptualization, Investigation, Methodology, Visualization, Writing-original draft. \u003cstrong\u003eDr. Fabio L P Costa\u003c/strong\u003e: Data curation, Writing-review editing. \u003cstrong\u003eDr. Gunar V S Mota\u003c/strong\u003e: Visualization, Writing-review editing.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgments\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThis work has been financially supported by CAPES for providing post-graduate scholarship and the Institute of Physics, University of Bras\u0026iacute;lia (UnB). In memory of Dra. Maria Suely P. Mundin (UnB).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData availability\u0026nbsp;\u003c/strong\u003eNot applicable.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eCode availability\u0026nbsp;\u003c/strong\u003eNot applicable.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eEthicsapproval \u0026nbsp;\u003c/strong\u003eNot applicable.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConsent to participate \u0026nbsp;\u0026nbsp;\u003c/strong\u003eNot applicable.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConsent for publication\u0026nbsp;\u003c/strong\u003eAll the authors gave their consent for publication.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflict of interest\u0026nbsp;\u003c/strong\u003eThe authors declare no competing interests.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eRosner, S., Cameron, R., Scholl, T., Holt, R.: A Study of the X 2Sigma\u0026thinsp;+\u0026thinsp;and A 2Pi States of SiO\u0026thinsp;+\u0026thinsp;Using Fast-Ion-Beam Laser Spectroscopy. 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After determining the structure and electronic energy of neutral and doubly ionized species, we used a new protocol based on the analysis of Wiberg's binding indexes and the quantum theory of atoms in Bader molecules (QTAIM). Where the charge transfer and electronic distribution in aromatic monomers indicate the possibility of fragment formation in at least two pairs of carbon-carbon (CC) atoms and indicate the possible loss of the -CNH\u003csub\u003e2\u003c/sub\u003e and -NO\u003csub\u003e2\u003c/sub\u003e groups in the aniline and nitroaniline molecules doubly ionized.\u003c/p\u003e","manuscriptTitle":"Fragmentation Route of doubly ionized benzene, aniline, and nitroanilines monomers using a novel protocol from density functional theory and QTAIM","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2022-07-22 17:45:26","doi":"10.21203/rs.3.rs-1825286/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Major revision","date":"2022-08-22T11:39:20+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2022-08-16T05:13:38+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"7a749002-a326-4b58-939c-ba0f9dcf8a5e","date":"2022-07-25T15:46:55+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2022-07-20T11:05:04+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2022-07-15T08:06:05+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2022-07-15T04:27:13+00:00","index":"","fulltext":""},{"type":"submitted","content":"Journal of Molecular Modeling","date":"2022-07-05T00:31:57+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"journal-of-molecular-modeling","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"jmmo","sideBox":"Learn more about [Journal of Molecular Modeling](https://www.springer.com/journal/894)","snPcode":"894","submissionUrl":"https://submission.nature.com/new-submission/894/3","title":"Journal of Molecular Modeling","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"878cc8c6-588a-46c2-8c93-c27b593e3cf2","owner":[],"postedDate":"July 22nd, 2022","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2023-10-16T18:36:19+00:00","versionOfRecord":{"articleIdentity":"rs-1825286","link":"https://doi.org/10.1007/s00894-023-05461-3","journal":{"identity":"journal-of-molecular-modeling","isVorOnly":false,"title":"Journal of Molecular Modeling"},"publishedOn":"2023-01-26 18:32:52","publishedOnDateReadable":"January 26th, 2023"},"versionCreatedAt":"2022-07-22 17:45:26","video":"","vorDoi":"10.1007/s00894-023-05461-3","vorDoiUrl":"https://doi.org/10.1007/s00894-023-05461-3","workflowStages":[]},"version":"v1","identity":"rs-1825286","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-1825286","identity":"rs-1825286","version":["v1"]},"buildId":"rHA-KDH7Qsr4HCuvH75dn","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}