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

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dc.contributor.authorThomas, LHen_AU
dc.contributor.authorJones, AOFen_AU
dc.contributor.authorKallay, AAen_AU
dc.contributor.authorMcIntyre, GJen_AU
dc.contributor.authorWilson, CCen_AU
dc.date.accessioned2021-12-17T03:38:21Zen_AU
dc.date.available2021-12-17T03:38:21Zen_AU
dc.date.issued2016-03-07en_AU
dc.date.statistics2021-12-07en_AU
dc.description.abstractA 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 Societyen_AU
dc.identifier.citationThomas, 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.5b01787en_AU
dc.identifier.issn1528-7505en_AU
dc.identifier.issue4en_AU
dc.identifier.journaltitleCrystal Growth & Designen_AU
dc.identifier.pagination2112-2122en_AU
dc.identifier.urihttps://doi.org/10.1021/acs.cgd.5b01787en_AU
dc.identifier.urihttps://apo.ansto.gov.au/dspace/handle/10238/12547en_AU
dc.identifier.volume16en_AU
dc.language.isoenen_AU
dc.publisherAmerican Chemical Societyen_AU
dc.subjectCovalenceen_AU
dc.subjectHydrogenen_AU
dc.subjectInteractionsen_AU
dc.subjectMoleculesen_AU
dc.subjectBenzoic aciden_AU
dc.subjectCarboxylic acidsen_AU
dc.titleEngineering short, strong, charge-assisted hydrogen bonds in benzoic acid dimers through cocrystallization with proton spongeen_AU
dc.typeJournal Articleen_AU
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