Unusual asymmetry in halobenzenes, a solid-state, gas-phase and theoretical investigation

S.L. Masters, I.D. MacKie, D.A. Wann, H.E. Robertson, D.W.H. Rankin, S. Parsons

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The molecular structures of 1-Br-4-F-C 6H 4 and 1-Cl-4-F-C 6H 4 have been studied in the gas phase using gas electron diffraction (GED) and ab initio methods. The structure of 1-Cl,4-F-C 6H 4 in the crystalline phase has also been studied, but whilst the gaseous structures were found to possess C 2v symmetry, the solid-state structure was found to be quite distorted, with three molecules in the asymmetric unit. These fragments only possess C s symmetry in the plane of the molecules, as opposed to the C 2v symmetry observed in the gas phase. The bonding motifs within the solid-state structure are very unusual and unexpected, with quite different C-F bond lengths for the three moieties, and are a result of weak hydrogen-halogen interactions within the structure. © 2010 Springer Science+Business Media, LLC.
Original languageEnglish
Pages (from-to)279-285
JournalStructural Chemistry
Issue number2
Publication statusPublished - Apr 2011

Bibliographical note

Cited By (since 1996):1

Export Date: 1 October 2013

Source: Scopus


doi: 10.1007/s11224-010-9700-0

Language of Original Document: English

Correspondence Address: Masters, S. L.; School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, United Kingdom; email: s.masters@ed.ac.uk

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  • Ab initio methods
  • Gas electron diffraction
  • Halobenzenes

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