Does intermolecular S=O?H–C–S=O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?

Brondel, Nicolas, Moynihan, Eamonn J.A., Lehane, K. Niamh, Eccles, Kevin S., Elcoate, Curtis J., Coles, Simon J., Lawrence, Simon E. and Maguire, Anita R. (2010) Does intermolecular S=O?H–C–S=O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state? CrystEngComm, 12 (10), 2910-2927. (doi:10.1039/c000371a).

Abstract

Hydrogen bonding between the sulfur oxygens and the acidic alpha-hydrogens in sulfoxides and sulfones is proposed as a supramolecular synthon in crystal engineering. A systematic analysis of supramolecular interactions in the solid state of a series of structurally related aryl benzyl sulfides, sulfoxides and sulfones was undertaken to establish the extent to which such hydrogen bonds persist as a structure determining feature in the solid state. The impact of the level of oxidation at sulfur, steric and electronic effects of substituents on the aryl rings and methyl substitution a to the sulfur functional group on the solid state structure of the compounds have been explored. The impact of stereochemical features, including relative and absolute stereochemistry, is also discussed.

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Contributors

Author: Simon J. Coles

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