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          Institute: MPI für bioanorganische Chemie     Collection: MPI für bioanorganische Chemie     Display Documents



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ID: 697881.0, MPI für bioanorganische Chemie / MPI für bioanorganische Chemie
Density Functional Study of Interactions between Fluorinated Cyclohexanes and Arenes
Authors:Cormanich, Rodrigo A.; Durie, Alastair; Bjornsson, Ragnar; Rittner, Roberto; O'Hagan, David; Bühl, Michael
Language:English
Date of Publication (YYYY-MM-DD):2014
Title of Journal:Helvetica Chimica Acta
Journal Abbrev.:Helv.Chim.Acta
Volume:97
Issue / Number:6
Start Page:797
End Page:807
Review Status:Peer-review
Audience:Experts Only
Abstract / Description: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.
External Publication Status:published
Document Type:Article
Communicated by:N. N.
Affiliations:MPI für bioanorganische Chemie
External Affiliations:[Cormanich,R.A.; Durie,A.; O'Hagan,D.; Bühl,M.]Univ St Andrews, EastChem Sch Chem, St Andrews KY16 9ST, Fife, Scotland.
[Rittner,R.] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil.
Identifiers:ISI:000337745600002 [ID No:1]
ISSN:0018-019X [ID No:2]
DOI:10.1002/hlca.201400049 [ID No:3]
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