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dc.contributor.authorCormanich, Rodrigo A.
dc.contributor.authorDurie, Alastair
dc.contributor.authorBjornsson, Ragnar
dc.contributor.authorRittner, Roberto
dc.contributor.authorO'Hagan, David
dc.contributor.authorBuehl, Michael
dc.date.accessioned2015-06-16T23:10:42Z
dc.date.available2015-06-16T23:10:42Z
dc.date.issued2014-06
dc.identifier.citationCormanich , 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.201400049en
dc.identifier.issn0018-019X
dc.identifier.otherPURE: 159999450
dc.identifier.otherPURE UUID: 6b3b55e5-7ed0-4bc4-8748-fb78013a1a6e
dc.identifier.otherWOS: 000337745600002
dc.identifier.otherScopus: 84902516918
dc.identifier.otherORCID: /0000-0002-1095-7143/work/48131781
dc.identifier.otherWOS: 000337745600002
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281305
dc.identifier.urihttp://hdl.handle.net/10023/6837
dc.descriptionThe 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.abstract1H-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.extent11
dc.language.isoeng
dc.relation.ispartofHelvetica Chimica Actaen
dc.rightsCopyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich. This is the accepted version of the following article: Cormanich, R. A., Durie, A., Bjornsson, R., Rittner, R., O'Hagan, D. and Bühl, M. (2014), Density Functional Study of Interactions between Fluorinated Cyclohexanes and Arenes. HCA, 97: 797–807., which has been published in final form at http://dx.doi.org/10.1002/hlca.201400049en
dc.subjectIntermolecular interactionsen
dc.subjectDesignen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleDensity functional study of interactions between fluorinated cyclohexanes and arenesen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1002/hlca.201400049
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-06-17
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/hlca.201400049/suppinfoen


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