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

Lynne H. Thomas, Andrew Owen Fletcher Jones, Andras A. Kallay, Garry J. McIntyre, Chick C. Wilson

Research output: Contribution to journalArticleResearchpeer-review


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).
Original languageEnglish
Pages (from-to)2112-2122
JournalCrystal growth & design
Issue number4
Publication statusPublished - 2016


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