| Full text | |
| Author(s): |
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
|
| Affiliation: | [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 |
| Abstract | |
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: | 11/01170-1 - Physicochemical studies of organic compounds: long range inractions and conformational analysis of organofluorine compounds. |
| Grantee: | Rodrigo Antonio Cormanich |
| Support Opportunities: | Scholarships in Brazil - Doctorate |
| 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 Opportunities: | Regular Research Grants |