Analysis of CF···FC interactions on cyclohexane and naphthalene frameworks

Rodrigo A. Cormanich, Roberto Rittner, David O'Hagan*, Michael Buehl

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)
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Abstract

Intramolecular CF···FC interactions in selected organofluorine compounds (all-syn-1,2,3,4- and all-syn-1,2,4,5-tetrafluorocyclohexane, 1,8-difluoronaphthalene, 4,5-difluorophenanthrene, 2,2′,5,5′-tetrafluorobiphenyl) were studied at the MP2/aug-cc-pVDZ level using the recently developed noncovalent interaction (NCI) method. For the optimized minima, all CF···FC interactions that are identified by this method are classified as attractive, even in those cases where suitable isodesmic reaction energies fail to provide evidence for an energetic stabilization. Possible relations between these interactions and the observable JFF spin–spin coupling constant values are discussed.

Original languageEnglish
Pages (from-to)7901-7910
Number of pages10
JournalJournal of Physical Chemistry A
Volume118
Issue number36
Early online date26 Aug 2014
DOIs
Publication statusPublished - 11 Sept 2014

Keywords

  • Nuclear-magnetic-resonance
  • Spin coupling-constants
  • Intermolecular interactions
  • Organofluorine chemistry
  • Molecular-structure
  • Electron-density
  • Fluorine
  • Bond
  • NMR
  • Atoms

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