Engineering short, strong, charge-assisted hydrogen bonds in benzoic acid dimers through co-crystallisation with proton sponge

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

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)
122 Downloads (Pure)

Abstract

A series of molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with mono-substituted 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 crystallisation ratio of 1:2 (DMAN:benzoic acid).
Original languageEnglish
Pages (from-to)2112-2122
JournalCrystal Growth and Design
Volume16
Issue number4
Early online date7 Mar 2016
DOIs
Publication statusPublished - 6 Apr 2016

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