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dc.contributor.authorJones, Mathew J.
dc.contributor.authorCallejo, Ricardo
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorBühl, Michael
dc.contributor.authorO'Hagan, David
dc.identifier.citationJones , M J , Callejo , R , Slawin , A M Z , Bühl , M & O'Hagan , D 2016 , ' Organofluorine chemistry : difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring ' , Beilstein Journal of Organic Chemistry , vol. 12 , pp. 2823-2827 .
dc.identifier.otherORCID: /0000-0002-1095-7143/work/48131760
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861830
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281271
dc.descriptionThis work was supported by the Engineering and Physical Sciences Research Council (EPSRC) and the European Research Council (ERC). The authors acknowledge the EPSRC National Mass Spectrometry Facility (Swansea). D.O’H. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstract2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF2 groups. The dipolar nature of the ring arises from the axial orientation of two of the C-F bonds pointing in the same direction, and set by the chair conformation of the cyclohexane. This electrostatic profile is revealed experimentally both in the solid-state (X-ray) packing of the rings and by solution (NMR) in different solvents. A computationally derived electrostatic profile of this compound is consistent with a more electronegative and a more electropositive face of the cyclohexane ring. This placing of CF2 groups 1,3 to each other in a cyclohexane ring is introduced as a new design strategy which could be applicable to the preparation of polar hydrophobic cyclohexane motifs.
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.subjectAliphatic ringsen
dc.subjectC-F bonden
dc.subjectCyclohexane conformationen
dc.subjectDifluoromethylene groupen
dc.subjectOrganofluorine chemistryen
dc.subjectQD Chemistryen
dc.subjectOrganic Chemistryen
dc.titleOrganofluorine chemistry : difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ringen
dc.typeJournal articleen
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.description.statusPeer revieweden

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