Utilizing sulfoxide···iodine halogen bonding for cocrystallization

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dc.contributor.authorEccles, Kevin S.
dc.contributor.authorMorrison, Robin E.
dc.contributor.authorStokes, Stephen P.
dc.contributor.authorO'Mahony, Graham E.
dc.contributor.authorHayes, John A.
dc.contributor.authorKelly, Dawn M.
dc.contributor.authorO'Boyle, Noel M.
dc.contributor.authorFábián, László
dc.contributor.authorMoynihan, Humphrey A.
dc.contributor.authorMaguire, Anita R.
dc.contributor.authorLawrence, Simon E.
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.contributor.funderHealth Research Boarden
dc.date.accessioned2013-01-23T21:58:34Z
dc.date.available2013-07-16T21:06:33Z
dc.date.issued2012-05
dc.date.updated2012-12-20T10:36:10Z
dc.description.abstractThe propensity of a range of different sulfoxides and sulfones to cocrystallize with either 1,2- or 1,4-diiodotetrafluorobenzene, via I•••O=S halogen bonding, was investigated. Cocrystallization occurred exclusively with 1,4-diiodotetrafluorobenzene in either a 1:1 or 1:2 stoichiometry of the organohalide and the sulfoxide, respectively, depending on the sulfoxide used. It was found that the stoichiometry observed was not necessarily related to whether the oxygen acts as a single halogen bond acceptor or if it is bifurcated; with I•••π interactions observed in two of the cocrystals synthesized. Only those cocrystals with a 1:2 stoichiometry exhibit C−H•••O hydrogen bonding in addition to I•••O=S halogen bonding. Examination of the Cambridge Structural Database shows that (i) the I•••O=S interaction is similar to other I•••O interactions, and (ii) the I•••π interaction is significant, with the distances in the two cocrystals among the shortest known.en
dc.description.sponsorshipScience Foundation Ireland (Grant Nos. 07/SRC/B1158); Science Foundation Ireland (05/PICA/B802 TIDA 09); Science Foundation Ireland (05/PICA/B802/EC07); Health Research Board (Career Development Fellowship PD/2009/13)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationEccles, Kevin; Morrison, Robin; Stokes, Stephen; O'Mahony, Graham; Hayes, John; Kelly, Dawn; O'Boyle, Noel; Fabian, Laszlo; Moynihan, H.; Maguire, Anita; Lawrence, Simon E. (2012) 'Utilizing Sulfoxide...Iodine Halogen Bonding for Cocrystallization'. Crystal Growth and Design, 12 (6):2969-2977. http://dx.doi.org/10.1021/cg300189ven
dc.identifier.doi10.1021/cg300189v
dc.identifier.endpage2977en
dc.identifier.issn1528-7483
dc.identifier.issued6en
dc.identifier.journaltitleCrystal Growth and Designen
dc.identifier.startpage2969en
dc.identifier.urihttps://hdl.handle.net/10468/920
dc.identifier.volume12en
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.rights© 2012, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth and 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/abs/10.1021/cg300189ven
dc.subjectSulfoxidesen
dc.subjectSulfonesen
dc.subjectCocrystallizationen
dc.subjectHalogen bondingen
dc.subjectOrganohalideen
dc.subjectStoichiometryen
dc.subject.lcshCrystallizationen
dc.titleUtilizing sulfoxide···iodine halogen bonding for cocrystallizationen
dc.typeArticle (peer-reviewed)en
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