Density functional study of interactions between fluorinated cyclohexanes and arenes

Rodrigo A. Cormanich, Alastair Durie, Ragnar Bjornsson, Roberto Rittner, David O'Hagan*, Michael Buehl

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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1H-NMR Chemical shifts of all-syn-1,2,4,5-tetrafluorocyclohexane (1), all-syn-1,2,3,4-tetrafluorocyclohexane (2), and their complexes with benzene are calculated at the BHandH/6-311+G(2d,p) level. The observed shielding of certain resonances on going from CD2Cl2 to (D8)toluene solution is qualitatively reproduced in these model calculations, in particular when standard B3LYP/def2-TZVP optimised geometries are employed. The results are interpreted with the quantum theory of atoms in molecules (QTAIM) and non-covalent interactions (NCI) methods, and they indicate that aromatic molecules bind strongly (1.6 kcal mol−1) to the ‘positive face’ of these molecules. The level of theory is validated for the new compound all-syn-1,2,4,5-tetrafluoro-3-phenylcyclohexane (3), where a recently developed QM/MM protocol for optimisation of molecular crystals afforded excellent agreement between the B3LYP/def2-TZVP structure and that observed in the solid.

Original languageEnglish
Pages (from-to)797-807
Number of pages11
JournalHelvetica Chimica Acta
Issue number6
Early online date17 Jun 2014
Publication statusPublished - Jun 2014


  • Intermolecular interactions
  • Design


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