Peer-Reviewed Journal Details
Mandatory Fields
By Eccles, Kevin S.; Morrison, Robin E.; Stokes, Stephen P.; O'Mahony, Graham E.; Hayes, John A.; Kelly, Dawn M.; O'Boyle, Noel M.; Fabian, Laszlo; Moynihan, Humphrey A.; Maguire, Anita R, Lawrence, Simon E.
2012
Crystal Growth & Design
Utilizing SulfoxideIodine Halogen Bonding for Cocrystallization
Published
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12
6
2969
2977
The propensity of a range of different sulfoxides and sulfones to cocrystallize with either 1,2- or 1,4-diiodotetrafluorobenzene, via IO=S halogen bonding, was investigated. Cocrystn. occurred exclusively with 1,4-diiodotetrafluorobenzene in either a 1:1 or 1:2 stoichiometry of the organohalide and the sulfoxide, resp., depending on the sulfoxide used. It was found that the stoichiometry obsd. was not necessarily related to whether the oxygen acts as a single halogen bond acceptor or if it is bifurcated; with Iπ interactions obsd. in two of the cocrystals synthesized. Only those cocrystals with a 1:2 stoichiometry exhibit C-HO hydrogen bonding in addn. to IO=S halogen bonding. Examn. of the Cambridge Structural Database shows that (i) the IO=S interaction is similar to other IO interactions, and (ii) the Iπ interaction is significant, with the distances in the two cocrystals among the shortest known.
DOI:10.1021/cg300189v
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