Unzipping the dimer in primary amides by cocrystallization with sulfoxides

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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.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.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.volume 11 en
dc.identifier.issued 10 en
dc.identifier.startpage 4433 en
dc.identifier.endpage 4439 en
dc.identifier.issn 1528-7483
dc.identifier.uri http://hdl.handle.net/10468/943
dc.identifier.doi 10.1021/cg2006277
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.format.mimetype application/pdf 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
dc.internal.authorurl http://research.ucc.ie/profiles/D004/slawrence en
dc.internal.authorcontactother Simon Lawrence, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: simon.lawrence@ucc.ie en
dc.internal.availability Full text available en
dc.date.updated 2012-12-21T10:10:05Z
dc.description.version Accepted Version en
dc.internal.rssid 117321851
dc.contributor.funder Science Foundation Ireland en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Crystal Growth & Design en
dc.internal.copyrightchecked Accepted Version - Include set statement - 12 month embargo after publishing date. en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en


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