An Overlooked Supramolecular Synthon in Multicomponent Trimethylglycine Crystals: Moderate Hydrogen Bonding Between Carboxylate and H-N Groups of Guanidine Species

Three novel multicomponent crystals of trimethylglycine with 2-cyanoguanidine, guanidinium and aminoguanidinium chlorides are synthesized and structurally characterized. All three crystal packings are based on the supramolecular synthon formed by two N–H groups of the guanidine species and carboxyla...

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Bibliographic Details
Main Authors: Andrei V. Churakov, Alexander G. Medvedev, Nikita E. Frolov, Mikhail V. Vener
Format: Article
Language:English
Published: MDPI AG 2024-11-01
Series:Crystals
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Online Access:https://www.mdpi.com/2073-4352/14/12/1050
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Summary:Three novel multicomponent crystals of trimethylglycine with 2-cyanoguanidine, guanidinium and aminoguanidinium chlorides are synthesized and structurally characterized. All three crystal packings are based on the supramolecular synthon formed by two N–H groups of the guanidine species and carboxylate group of trimethylglycine (graph set notation R<sup>2</sup><sub>2</sub>(8)). Its enthalpy is about 50 kJ/mol. The three-dimensional structure of crystals is stabilized by intermolecular interactions of various types. The energy of C–H∙∙∙X<sup>−</sup> interactions, where X = O, Cl, reaches 16 kJ/mol due to the acidic nature of methyl hydrogens. The possible structure of the trimethylglycine–urea–2H<sub>2</sub>O complex is discussed. Its theoretical metric and spectroscopic parameters are in reasonable agreement with the available literature data on the deep eutectic solvent trimethylglycine–urea.
ISSN:2073-4352