The X-ray Structures of Sulfones

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• 作者：Fiona A. M. Rudolph ; Amy L. Fuller ; Alexandra M. Z. Slawin ; Michael B¨¹hl ; R. Alan Aitken and J. Derek Woollins
• 关键词：Sulfone ; Structure ; Hydrogen bond ; Conformation
• 刊名：Journal of Chemical Crystallography
• 出版年：2010
• 出版时间：March, 2010
• 年：2010
• 卷：40
• 期：3
• 页码：253-265
• 全文大小：890.1 KB

文摘

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) Å and S–C bond distances range from 1.743(7) to 1.790(3) Å. The C–S–C bond angles vary from 101.1(3)¡ã to 106.80(14)¡ã and the O–S–O bond angles vary from 116.7(2)¡ã to 120.61(8)¡ã. 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.