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Crystals 2018, 8(3), 132; https://doi.org/10.3390/cryst8030132

Experimental Electron Density Distribution in Two Cocrystals of Betaines with p-Hydroxybenzoic Acid

Department of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland
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Received: 8 February 2018 / Revised: 5 March 2018 / Accepted: 8 March 2018 / Published: 10 March 2018
(This article belongs to the Special Issue Experimental and Theoretical Electron Density Analysis of Crystals)
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Abstract

Experimental determination of electron density distribution in crystals by means of high-resolution X-ray diffraction allows, among others, for studying the details of intra- and inter-molecular interactions. In case of co-crystals, this method may help in finding the conditions of creating such species. The results of such analysis for two co-crystals containing betaines, namely trigonelline (TRG: nicotinic acid N-methylbetaine, IUPAC name: 1-methylpyridinium-3-carboxylate) and N-methylpiperidine betaine (MPB: 1-methylpiperidinium-1-yl-carboxylate) with p-hydroxybenzoic acid (HBA) are reported. TRG-HBA crystallizes as a hydrate. For both of the co-crystals, high-quality diffraction data were collected up to sinθ/λ = 1.13 Å−1. Hansen-Coppens multipolar model was then applied for modelling the electron density distribution and Atoms-In-Molecules approach was used for detailed analysis of interactions in crystals. A number of intermolecular interactions was identified, ranging from strong O-H···O hydrogen bonds through C-H···O to C-H···π and π···π interactions. Correlations between the geometrical characteristics of the contacts and the features of their critical points were analyzed in detail. Atomic charges show that in zwitterionic species there are regions of opposite charges, rather than charges that are localized on certain atoms. In case of MPB-HBA, a significant charge transfer between the components of co-crystal (0.5 e) was found, as opposed to TRG-HBA, where all of the components are almost neutral. View Full-Text
Keywords: electron density; betaine; trigonelline; zwitterion; topological analysis; hydrogen bond; non-covalent interactions electron density; betaine; trigonelline; zwitterion; topological analysis; hydrogen bond; non-covalent interactions
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Owczarzak, A.; Kubicki, M. Experimental Electron Density Distribution in Two Cocrystals of Betaines with p-Hydroxybenzoic Acid. Crystals 2018, 8, 132.

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