All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane

Neil S. Keddie, Alexandra M.Z. Slawin, Tomas Lebl, Douglas Philp, David O'Hagan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

85 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)483-488
Number of pages6
JournalNature chemistry
Volume7
Issue number6
DOIs
StatePublished - Jun 26 2015

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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