Unzipping the dimer in primary amides by cocrystallization with sulfoxides
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Accepted Version
Supporting Data
Date
2011-01
Authors
Eccles, Kevin S.
Elcoate, Curtis J.
Maguire, Anita R.
Lawrence, Simon E.
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Published Version
Abstract
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.
Description
Keywords
Crystal engineering , Aromatic amides , Cocrystallize , Dibenzyl sulfoxide , Synthons , Dimer
Citation
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
Copyright
© 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