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- Title
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
- Abstract
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.
- Subjects
CHEMICAL shift (Nuclear magnetic resonance); BENZENE; TOLUENE; MOLECULAR crystals; QUANTUM theory; FLUORINATION; CYCLOHEXANE; AROMATIC compounds
- Publication
Helvetica Chimica Acta, 2014, Vol 97, Issue 6, p797
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201400049