{"paper_id":"474db9eb-e12f-4640-a773-ce373c1ed2e4","body_text":"Short halogen-carbon bonds in 1-chloro- and 1-bromo-1-nitro-2,3-difluorocyclopropanes: Synergistic 1,4-intramolecular interactions? | 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 Short halogen-carbon bonds in 1-chloro- and 1-bromo-1-nitro-2,3-difluorocyclopropanes: Synergistic 1,4-intramolecular interactions? Ponnadurai Ramasami, Goedele Roos, Jane S. Murray This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7452553/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 22 Oct, 2025 Read the published version in Structural Chemistry → Version 1 posted 7 You are reading this latest preprint version Abstract Cyclopropane is introduced in this computational study as a framework for obtaining contracted carbon-chlorine and carbon-bromine bond lengths, utilizing the M06-2X/aug-cc-pVTZ method/basis set combination. For chloro- and bromocyclopropane, placing a nitro group on the same carbon as the chlorine or bromine and two fluorines in the 2 and 3 positions closest to the larger halogen leads to three 1—4 intramolecular interactions with the chloro and bromo substituents, with computed C-Cl and C-Br bond lengths of 1.711 Å and 1.872 Å, respectively. Adding more fluorines to this framework does not lead to shorter carbon-chlorine or carbon-bromine bond lengths because of the what has been labeled the “Teflon” effect; as more fluorines are added they become less negative or even positive. The Coulombic interpretation of the above-mentioned bond contractions is supported by computed electrostatic potentials. intramolecular interactions chloro- and bromo-cyclopropanes nitro and fluoro substitution contracted C-X bond lengths Coulombic interactions Full Text Additional Declarations No competing interests reported. Cite Share Download PDF Status: Published Journal Publication published 22 Oct, 2025 Read the published version in Structural Chemistry → Version 1 posted Editorial decision: Revision requested 23 Sep, 2025 Reviews received at journal 22 Sep, 2025 Reviewers agreed at journal 01 Sep, 2025 Reviewers invited by journal 29 Aug, 2025 Editor assigned by journal 29 Aug, 2025 Submission checks completed at journal 28 Aug, 2025 First submitted to journal 25 Aug, 2025 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. 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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-7452553\",\"acceptedTermsAndConditions\":true,\"allowDirectSubmit\":false,\"archivedVersions\":[],\"articleType\":\"Research Article\",\"associatedPublications\":[],\"authors\":[{\"id\":508687145,\"identity\":\"bb219dd5-c51e-4eef-8acc-97a2b7db61b1\",\"order_by\":0,\"name\":\"Ponnadurai Ramasami\",\"email\":\"\",\"orcid\":\"\",\"institution\":\"University of Mauritius\",\"correspondingAuthor\":false,\"prefix\":\"\",\"firstName\":\"Ponnadurai\",\"middleName\":\"\",\"lastName\":\"Ramasami\",\"suffix\":\"\"},{\"id\":508687146,\"identity\":\"8498ac91-50d8-4bc1-af34-8d58b7206a1d\",\"order_by\":1,\"name\":\"Goedele Roos\",\"email\":\"\",\"orcid\":\"\",\"institution\":\"Univ. 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For chloro- and bromocyclopropane, placing a nitro group on the same carbon as the chlorine or bromine and two fluorines in the 2 and 3 positions closest to the larger halogen leads to three 1\\u0026mdash;4 intramolecular interactions with the chloro and bromo substituents, with computed C-Cl and C-Br bond lengths of 1.711 \\u0026Aring; and 1.872 \\u0026Aring;, respectively. Adding more fluorines to this framework does not lead to shorter carbon-chlorine or carbon-bromine bond lengths because of the what has been labeled the \\u0026ldquo;Teflon\\u0026rdquo; effect; as more fluorines are added they become less negative or even positive. The Coulombic interpretation of the above-mentioned bond contractions is supported by computed electrostatic potentials.\\u003c/p\\u003e\",\"manuscriptTitle\":\"Short halogen-carbon bonds in 1-chloro- and 1-bromo-1-nitro-2,3-difluorocyclopropanes: Synergistic 1,4-intramolecular interactions?\",\"msid\":\"\",\"msnumber\":\"\",\"nonDraftVersions\":[{\"code\":1,\"date\":\"2025-09-05 20:36:39\",\"doi\":\"10.21203/rs.3.rs-7452553/v1\",\"editorialEvents\":[{\"type\":\"communityComments\",\"content\":0},{\"type\":\"decision\",\"content\":\"Revision requested\",\"date\":\"2025-09-23T06:11:14+00:00\",\"index\":\"\",\"fulltext\":\"\"},{\"type\":\"editorInvitedReview\",\"content\":\"\",\"date\":\"2025-09-22T13:05:39+00:00\",\"index\":\"hide\",\"fulltext\":\"\"},{\"type\":\"reviewerAgreed\",\"content\":\"184202504124805822994114034169140183134\",\"date\":\"2025-09-01T17:45:14+00:00\",\"index\":\"hide\",\"fulltext\":\"\"},{\"type\":\"reviewersInvited\",\"content\":\"\",\"date\":\"2025-08-29T04:17:01+00:00\",\"index\":\"\",\"fulltext\":\"\"},{\"type\":\"editorAssigned\",\"content\":\"\",\"date\":\"2025-08-29T04:14:39+00:00\",\"index\":\"\",\"fulltext\":\"\"},{\"type\":\"checksComplete\",\"content\":\"\",\"date\":\"2025-08-28T09:19:22+00:00\",\"index\":\"\",\"fulltext\":\"\"},{\"type\":\"submitted\",\"content\":\"Structural Chemistry\",\"date\":\"2025-08-25T09:57:23+00:00\",\"index\":\"\",\"fulltext\":\"\"}],\"status\":\"published\",\"journal\":{\"display\":true,\"email\":\"info@researchsquare.com\",\"identity\":\"structural-chemistry\",\"isNatureJournal\":false,\"hasQc\":true,\"allowDirectSubmit\":false,\"externalIdentity\":\"stuc\",\"sideBox\":\"Learn more about [Structural Chemistry](https://www.springer.com/journal/11224)\",\"snPcode\":\"11224\",\"submissionUrl\":\"https://submission.nature.com/new-submission/11224/3\",\"title\":\"Structural Chemistry\",\"twitterHandle\":\"\",\"acdcEnabled\":true,\"dfaEnabled\":true,\"editorialSystem\":\"em\",\"reportingPortfolio\":\"Springer Hybrid\",\"inReviewEnabled\":true,\"inReviewRevisionsEnabled\":false}}],\"origin\":\"\",\"ownerIdentity\":\"8056f1c2-3659-46da-bafa-39a61e842085\",\"owner\":[],\"postedDate\":\"September 5th, 2025\",\"published\":true,\"recentEditorialEvents\":[],\"rejectedJournal\":[],\"revision\":\"\",\"amendment\":\"\",\"status\":\"published-in-journal\",\"subjectAreas\":[],\"tags\":[],\"updatedAt\":\"2025-10-27T16:25:53+00:00\",\"versionOfRecord\":{\"articleIdentity\":\"rs-7452553\",\"link\":\"https://doi.org/10.1007/s11224-025-02639-8\",\"journal\":{\"identity\":\"structural-chemistry\",\"isVorOnly\":false,\"title\":\"Structural Chemistry\"},\"publishedOn\":\"2025-10-22 16:17:15\",\"publishedOnDateReadable\":\"October 22nd, 2025\"},\"versionCreatedAt\":\"2025-09-05 20:36:39\",\"video\":\"\",\"vorDoi\":\"10.1007/s11224-025-02639-8\",\"vorDoiUrl\":\"https://doi.org/10.1007/s11224-025-02639-8\",\"workflowStages\":[]},\"version\":\"v1\",\"identity\":\"rs-7452553\",\"journalConfig\":\"researchsquare\"},\"__N_SSP\":true},\"page\":\"/article/[identity]/[[...version]]\",\"query\":{\"redirect\":\"/article/rs-7452553\",\"identity\":\"rs-7452553\",\"version\":[\"v1\"]},\"buildId\":\"8U1c8b4HqxoKbykW_rLl7\",\"isFallback\":false,\"isExperimentalCompile\":false,\"dynamicIds\":[84888],\"gssp\":true,\"scriptLoader\":[]}","source_license":"CC-BY-4.0","license_restricted":false}