Utilizing Sulfoxide路路路Iodine Halogen Bonding for Cocrystallization

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• 作者：Kevin S. Eccles ; Robin E. Morrison ; Stephen P. Stokes ; Graham E. O鈥橫ahony ; John A. Hayes ; Dawn M. Kelly ; Noel M. O鈥橞oyle ; L谩szl贸 F谩bi谩n ; Humphrey A. Moynihan ; Anita R. Maguire ; Simon E. Lawrence
• 刊名：Crystal Growth & Design
• 出版年：2012
• 出版时间：June 6, 2012
• 年：2012
• 卷：12
• 期：6
• 页码：2969-2977
• 全文大小：452K
• 年卷期：v.12,no.6(June 6, 2012)
• ISSN：1528-7505

文摘

The propensity of a range of different sulfoxides and sulfones to cocrystallize with either 1,2- or 1,4-diiodotetrafluorobenzene, via I路路路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路路路蟺 interactions observed in two of the cocrystals synthesized. Only those cocrystals with a 1:2 stoichiometry exhibit C鈥揌路路路O hydrogen bonding in addition to I路路路O=S halogen bonding. Examination of the Cambridge Structural Database shows that (i) the I路路路O=S interaction is similar to other I路路路O interactions, and (ii) the I路路路蟺 interaction is significant, with the distances in the two cocrystals among the shortest known.