Utilizing sulfoxide···iodine halogen bonding for cocrystallization

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Eccles, Kevin S.
Morrison, Robin E.
Stokes, Stephen P.
O'Mahony, Graham E.
Hayes, John A.
Kelly, Dawn M.
O'Boyle, Noel M.
Fábián, László
Moynihan, Humphrey A.
Maguire, Anita R.
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American Chemical Society
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The 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.
Sulfoxides , Sulfones , Cocrystallization , Halogen bonding , Organohalide , Stoichiometry
Eccles, 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/cg300189v
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© 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/cg300189v