Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge

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• 作者：Lynne H. Thomas ; Andrew O. F. Jones ; Andras A. Kallay ; Garry J. McIntyre ; Chick C. Wilson
• 刊名：Crystal Growth & Design
• 出版年：2016
• 出版时间：April 6, 2016
• 年：2016
• 卷：16
• 期：4
• 页码：2112-2122
• 全文大小：582K
• ISSN：1528-7505

文摘

A series of molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with monosubstituted halobenzoic acids are reported, illustrating the designed exploitation of the characteristics of the proton sponge to induce short, charge-assisted hydrogen bonds in a predictable and reproducible manner. In every case, a DMAN molecule extracts a proton from the carboxylic acid group of the benzoic acid, as a result of which a recurrent supramolecular unit between a neutral and a deprotonated benzoic acid molecule is formed, featuring an extremely short, strong O–H···O hydrogen bond, within a predominant crystallization ratio of 1:2 (DMAN:benzoic acid).