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Density functional study of interactions between fluorinated cyclohexanes and arenes
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dc.contributor.author | Cormanich, Rodrigo A. | |
dc.contributor.author | Durie, Alastair | |
dc.contributor.author | Bjornsson, Ragnar | |
dc.contributor.author | Rittner, Roberto | |
dc.contributor.author | O'Hagan, David | |
dc.contributor.author | Buehl, Michael | |
dc.date.accessioned | 2015-06-16T23:10:42Z | |
dc.date.available | 2015-06-16T23:10:42Z | |
dc.date.issued | 2014-06 | |
dc.identifier | 159999450 | |
dc.identifier | 6b3b55e5-7ed0-4bc4-8748-fb78013a1a6e | |
dc.identifier | 000337745600002 | |
dc.identifier | 84902516918 | |
dc.identifier | 000337745600002 | |
dc.identifier.citation | Cormanich , R A , Durie , A , Bjornsson , R , Rittner , R , O'Hagan , D & Buehl , M 2014 , ' Density functional study of interactions between fluorinated cyclohexanes and arenes ' , Helvetica Chimica Acta , vol. 97 , no. 6 , pp. 797-807 . https://doi.org/10.1002/hlca.201400049 | en |
dc.identifier.issn | 0018-019X | |
dc.identifier.other | ORCID: /0000-0002-1095-7143/work/48131781 | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/68281305 | |
dc.identifier.uri | https://hdl.handle.net/10023/6837 | |
dc.description | The authors thank a Grant # 2012/03933-5, Sao Paulo Research Foundation (FAPESP), for providing financial support for this research, for a scholarship (to R.A.C. #2011/01170-1, FAPESP). CNPq is also acknowledged for a fellowship (to R.R) and a studentship (to R.A.C.). We thank the Royal Society (Wolfson Merit Award for D.O' H.) and EaStCHEM (support for M.B. and access to a computing facility maintained by H. Fruchtl). | en |
dc.description.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. | |
dc.format.extent | 11 | |
dc.format.extent | 734331 | |
dc.language.iso | eng | |
dc.relation.ispartof | Helvetica Chimica Acta | en |
dc.subject | Intermolecular interactions | en |
dc.subject | Design | en |
dc.subject | QD Chemistry | en |
dc.subject.lcc | QD | en |
dc.title | Density functional study of interactions between fluorinated cyclohexanes and arenes | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.1002/hlca.201400049 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2015-06-17 | |
dc.identifier.url | http://onlinelibrary.wiley.com/doi/10.1002/hlca.201400049/suppinfo | en |
dc.identifier.grantnumber | EP/H022651/1 | en |
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