Tris(hydroxymethyl)methyl ammonium salts of biologically active carboxylic acids. Synthesis, properties and crystal structure

• Published in: Journal of molecular structure Vol. 1207; p. 127813
• Main Authors: Kondratenko, Yu.A., Nikonorova, A.A., Zolotarev, A.A., Ugolkov, V.L., Kochina, T.A.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05-05-2020
• Subjects: Antimicrobial activity; Crystal structure; Protic ionic liquids; Synthesis; Thermal stability; Tromethamine; Antimicrobial activity; Synthesis; Thermal stability; Protic ionic liquids; Tromethamine; Crystal structure
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.127813

Tris(hydroxymethyl)methyl ammonium salts, [C(CH2OH)3NH3]X, were obtained for the first time by the interaction of tris(hydroxymethyl)aminomethane (TRIS) with carboxylic acids (cinnamic, benzoic, salicylic, nicotinic, 2-methylphenoxyacetic, succinic, malonic, oxalic, malic and citric). The new compounds (1–15) were characterized by 1H NMR, 13C NMR, FT-IR, elemental analysis and thermal analysis methods. The crystal structures of the tris(hydroxymethyl)methyl ammonium hydrogen malonate, hydrogen succinate and 2-methylphenoxyacetate were determined by the single-crystal X-ray diffraction. The antimicrobial activity of some synthesized tris(hydroxymethyl)methyl ammonium salts against bacteria Escherichia coli, Staphylococcus aureus, Mycobacterium tuberculosis and fungi Candida albicans and Aspergillus niger has been investigated.
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•15 Tris (hydroxymethyl)methyl ammonium salts of biologically active carboxylic acids were synthesized and characterized.•Three conformations (“planar”, “exo-” and “endo-exo”- conformations) are characteristic of TRIS cations; .•The “planar” conformation is the most typical conformation for TRIS salts•TRIS salts of malonic, malic and citric acids can be attributed to the class of PILs.•Some of TRIS salts are active against the bacterium Mycobacterium tuberculosis and the fungus Aspergillus niger.