Brondel, N;Moynihan, EJA;Lehane, KN;Eccles, KS;Elcoate, CJ;Coles, SJ;Lawrence, SE;Maguire, AR

2010

January

Crystengcomm

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

Validated

WOS: 16 ()

CRYSTAL-STRUCTURES TERMINAL ALKYNES DATABASE COMPLEXES MOLECULES CHEMISTRY

12

2910

2927

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.

CAMBRIDGE

1466-8033

10.1039/c000371a