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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Density Functional Study of Interactions between Fluorinated Cyclohexanes and Arenes

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Cormanich, Rodrigo A. [1, 2, 3] ; Durie, Alastair [2, 3] ; Bjornsson, Ragnar [4] ; Rittner, Roberto [1] ; O'Hagan, David [2, 3] ; Buehl, Michael [2, 3]
Total Authors: 6
[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil
[2] Univ St Andrews, EastChem Sch Chem, St Andrews KY16 9ST, Fife - Scotland
[3] Univ St Andrews, Ctr Magnet Resonance, St Andrews KY16 9ST, Fife - Scotland
[4] MPI Chem Energy Convers, D-45470 Mulheim - Germany
Total Affiliations: 4
Document type: Journal article
Source: Helvetica Chimica Acta; v. 97, n. 6, p. 797-807, JUN 2014.
Web of Science Citations: 5

H-1-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 (D-8) 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. (AU)

FAPESP's process: 12/03933-5 - Conformational equilibria and intramolecular interactions for a series of amino-acids: theoretical and experimental approaches
Grantee:Roberto Rittner Neto
Support type: Regular Research Grants
FAPESP's process: 11/01170-1 - Physicochemical studies of organic compounds: long range inractions and conformational analysis of organofluorine compounds.
Grantee:Rodrigo Antonio Cormanich
Support type: Scholarships in Brazil - Doctorate