Unzipping the dimer in primary amides by cocrystallization with sulfoxides

Eccles, Kevin S.; Elcoate, Curtis J.; Maguire, Anita R.; Lawrence, Simon E.

Unzipping the dimer in primary amides by cocrystallization with sulfoxides

dc.contributor.author	Eccles, Kevin S.
dc.contributor.author	Elcoate, Curtis J.
dc.contributor.author	Maguire, Anita R.
dc.contributor.author	Lawrence, Simon E.
dc.contributor.funder	Science Foundation Ireland	en
dc.date.accessioned	2013-01-30T11:05:46Z
dc.date.available	2013-01-30T11:05:46Z
dc.date.copyright	2011
dc.date.issued	2011-01
dc.date.updated	2012-12-21T10:10:05Z
dc.description.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.	en
dc.description.sponsorship	Science Foundation Ireland (08/RFP/MTR1664); Science Foundation Ireland (07/SRC/B1158); Science Foundation Ireland (05/PICA/B802/EC07)	en
dc.description.status	Peer reviewed	en
dc.description.version	Accepted Version	en
dc.format.mimetype	application/pdf	en
dc.identifier.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	en
dc.identifier.doi	10.1021/cg2006277
dc.identifier.endpage	4439	en
dc.identifier.issn	1528-7483
dc.identifier.issued	10	en
dc.identifier.journaltitle	Crystal Growth & Design	en
dc.identifier.startpage	4433	en
dc.identifier.uri	https://hdl.handle.net/10468/943
dc.identifier.volume	11	en
dc.language.iso	en	en
dc.publisher	American Chemical Society	en
dc.relation.uri	http://pubs.acs.org/doi/full/10.1021/cg2006277
dc.rights	© 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	en
dc.subject	Crystal engineering	en
dc.subject	Aromatic amides	en
dc.subject	Cocrystallize	en
dc.subject	Dibenzyl sulfoxide	en
dc.subject	Synthons	en
dc.subject	Dimer	en
dc.subject.lcsh	Crystallization	en
dc.title	Unzipping the dimer in primary amides by cocrystallization with sulfoxides	en
dc.type	Article (peer-reviewed)	en