Engineering short, strong, charge-assisted hydrogen bonds in benzoic acid dimers through cocrystallization with proton sponge
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Date
2016-03-07
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Abstract
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). © 2016 American Chemical Society
Description
Keywords
Covalence, Hydrogen, Interactions, Molecules, Benzoic acid, Carboxylic acids
Citation
Thomas, L. H., Jones, A. O. F., Kallay, A. A., McIntyre, G. J., & Wilson, C. C. (2016). Engineering short, strong, charge-assisted hydrogen bonds in benzoic acid dimers through cocrystallization with proton sponge. Crystal Growth & Design, 16(4), 2112–2122. doi:10.1021/acs.cgd.5b01787