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Title:Utilizing Sulfoxide...Iodine Halogen Bonding for Cocrystallization
Authors:Kevin S. Eccles, Robin E. Morrison, Stephen P. Stokes, Graham E. O’Mahony, John A. Hayes, Dawn M. Kelly, Noel M. O'Boyle, László Fábián, Humphrey A. Moynihan, Anita R. Maguire, and Simon E. Lawrence, 2012
Abstract: 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.
ICHEC Project:Computational investigation of Cu-catalysed intramolecular C–H insertion reactions
Publication:Cryst. Growth Des., Article ASAP, May 2012
URL: http://pubs.acs.org/doi/abs/10.1021/cg300189v
Keywords: computational chemistry;molecular design
Status: Published

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