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dc.contributor.authorKeddie, Neil Steven
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorLebl, Tomas
dc.contributor.authorPhilp, Douglas
dc.contributor.authorO'Hagan, David
dc.identifier.citationKeddie , N S , Slawin , A M Z , Lebl , T , Philp , D & O'Hagan , D 2015 , ' All- cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane ' , Nature Chemistry , vol. 7 , no. 6 , pp. 483-488 .
dc.identifier.otherPURE: 174240424
dc.identifier.otherPURE UUID: 06dab60c-a62d-40a7-8313-338bad4b0e11
dc.identifier.otherScopus: 84930198476
dc.identifier.otherORCID: /0000-0002-0269-3221/work/48131719
dc.identifier.otherORCID: /0000-0002-9198-4302/work/56639226
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861433
dc.identifier.otherORCID: /0000-0002-9502-5862/work/35745202
dc.identifier.otherWOS: 000354799800007
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281218
dc.descriptionThis work was generously supported by the Engineering and Physical Sciences Research Council (EPSRC) and the European Research Council (ERC).en
dc.description.abstractThe highest-energy stereoisomer of 1,2,3,4,5,6-hexafluorocyclohexane, in which all of the fluorines are ‘up’, is prepared in a 12-step protocol. The molecule adopts a classic chair conformation with alternate C–F bonds aligned triaxially, clustering three highly electronegative fluorine atoms in close proximity. This generates a cyclohexane with a high molecular dipole (μ = 6.2 D), unusual in an otherwise aliphatic compound. X-ray analysis indicates that the intramolecular Fax···Fax distances (∼2.77 Å) are longer than the vicinal Fax···Feq­ distances (∼2.73 Å) suggesting a tension stabilizing the chair conformation. In the solid state the molecules pack in an orientation consistent with electrostatic ordering. Our synthesis of this highest-energy isomer demonstrates the properties that accompany the placement of axial fluorines on a cyclohexane and the unusual property of a facially polarized ring in organic chemistry. Derivatives have potential as new motifs for the design of functional organic molecules or for applications in supramolecular chemistry design.
dc.relation.ispartofNature Chemistryen
dc.rights© 2015 the Author(s). This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at
dc.subjectQD Chemistryen
dc.titleAll-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexaneen
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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