The X-ray Structures of Sulfones

Fiona A. M. Rudolph, Amy L. Fuller, Alexandra M. Z. Slawin, Michael Buehl, R. Alan Aitken, J. Derek Woollins

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

The X-rays structures of diphenyl sulfone 1, bis(3-aminophenyl) sulfone 2, bis(4-nitrophenyl) sulfone 3, 2-nitrophenylphenyl sulfone 4, benzylphenzyl sulfone 5, 4-nitrobenzylphenyl sulfone 6, 4-methylphenylbenzyl sulfone 7, dibenzyl sulfone 8, benzylisopropyl sulfone 9, and methylacetate, ethyl sulfone 10, are reported. B3PW91 DFT calculations were performed on selected sulfones for comparison. The S = O distances in these compounds range from 1.392(5) to 1.463(3) angstrom and S-C bond distances range from 1.743(7) to 1.790(3) angstrom. The C-S-C bond angles vary from 101.1(3)degrees to 106.80(14)degrees and the O-S-O bond angles vary from 116.7(2)degrees to 120.61(8)degrees. Using data obtained here and comparison with published structural data no evidence was found for para substituents on aryl groups influencing S-O bond distances, however, small changes on S-C bond distances were noted. Additionally, if the sulfur is flanked by an alkyl group the S-C distance is slightly larger than when it is flanked by an aryl group. Most of the sulfone compounds studied here display intermolecular soft hydrogen bonding interactions which influence their solid state packing. Furthermore, in dialkyl sulfone compounds these interactions appear to be strong enough to overcome conformational barriers calculated to be ca. 6 kJ mol(-1).

Original languageEnglish
Pages (from-to)253-265
Number of pages13
JournalJournal of Chemical Crystallography
Volume40
Issue number3
DOIs
Publication statusPublished - Mar 2010

Keywords

  • Sulfone
  • Structure
  • Hydrogen bond
  • Conformation
  • SULFOXIDES
  • OXIDATION
  • NETS

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