Unzipping the dimer in primary amides by cocrystallization with sulfoxides

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Eccles, Kevin S.
Elcoate, Curtis J.
Maguire, Anita R.
Lawrence, Simon E.
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American Chemical Society
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A systematic crystal engineering study was undertaken to investigate how different electronic substituents on the aromatic ring of primary aromatic amides impact on the ability of the amide to cocrystallize with dibenzyl sulfoxide. Amides which cocrystallize with dibenzyl sulfoxide form 1:1 cocrystals containing a discrete N-H•••O=S supramolecular synthon as well as the well-known C(4) amide chain. The combination of these two synthons give rise to linear chains of amide molecules, with each amide molecule capped by one sulfoxide molecule. Thus, the R 2(over)2 (8) dimer typically seen for primary amides is no longer present in these cocrystals. The influence of the amide due to electronic effects is similar to that observed for acids in cocrystals.
Crystal engineering , Aromatic amides , Cocrystallize , Dibenzyl sulfoxide , Synthons , Dimer
Eccles, Kevin S., Elcoate, Curtis J., Maguire, Anita R., Lawrence, Simon E. (2011) 'Unzipping the Dimer in Primary Amides by Cocrystallization with Sulfoxides'. Crystal Growth & Design, 11 (10):4433-4439. http://pubs.acs.org/doi/full/10.1021/cg2006277
© 2011 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth & Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/full/10.1021/cg2006277