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All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane
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dc.contributor.author | Keddie, Neil Steven | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Lebl, Tomas | |
dc.contributor.author | Philp, Douglas | |
dc.contributor.author | O'Hagan, David | |
dc.date.accessioned | 2015-10-12T23:11:39Z | |
dc.date.available | 2015-10-12T23:11:39Z | |
dc.date.issued | 2015-06 | |
dc.identifier | 174240424 | |
dc.identifier | 06dab60c-a62d-40a7-8313-338bad4b0e11 | |
dc.identifier | 84930198476 | |
dc.identifier | 000354799800007 | |
dc.identifier.citation | Keddie , 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 . https://doi.org/10.1038/nchem.2232 | en |
dc.identifier.issn | 1755-4330 | |
dc.identifier.other | ORCID: /0000-0002-0269-3221/work/48131719 | |
dc.identifier.other | ORCID: /0000-0002-9198-4302/work/56639226 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861433 | |
dc.identifier.other | ORCID: /0000-0002-9502-5862/work/35745202 | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/68281218 | |
dc.identifier.uri | https://hdl.handle.net/10023/7647 | |
dc.description | This work was generously supported by the Engineering and Physical Sciences Research Council (EPSRC) and the European Research Council (ERC). | en |
dc.description.abstract | The 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.format.extent | 6498813 | |
dc.language.iso | eng | |
dc.relation.ispartof | Nature Chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | BDC | en |
dc.subject | R2C | en |
dc.subject.lcc | QD | en |
dc.title | All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | 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 | 10.1038/nchem.2232 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2015-10-13 | |
dc.identifier.grantnumber | EP/F03055X/1 | en |
dc.identifier.grantnumber | EP/H022651/1 | en |
dc.identifier.grantnumber | EP/K039210/1 | en |
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