Complexes of Nitrilotriacetic Acid with Amines. Molecular Structures of 2-Ammonioethanol Nitrilotriacetate and Bis{2-Ammonio-2-(Hydroxymethyl)propane-1,3-Diol} Nitrilotriacetate

• Published in: Crystallography reports Vol. 66; no. 3; pp. 441 - 447
• Main Authors: Rumyantcev, R. V., Zolotareva, N. V., Novikova, O. V., Petrov, B. I., Lazarev, N. M., Semenov, V. V.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.05.2021; Springer Nature B.V
• Subjects: Acids; Amines; Chains (polymeric); Crystallography and Scattering Methods; Hydrogen bonds; Molecular structure; Nitrilotriacetic acid; Physics; Physics and Astronomy; Polymers; Propane; Structure of Organic Compounds
• ISSN: 1063-7745; 1562-689X
• DOI: 10.1134/S1063774521030214

Reactions of nitrilotriacetic acid with 2-aminoethanol, 2-amino-2-(hydroxymethyl)propane-1,3-diol, and 2,2'-(ethylenedioxy)bis(ethylamine) afford the following salts in high yields: 2-ammonioethanol nitrilotriacetate [HN + (CH 2 COO – ) 2 (CH 2 COOH) ⋅ H 3 N + CH 2 CH 2 OH] n , bis{2-ammonio-2-(hydroxymethyl)propane-1,3-diol} nitrilotriacetate HN + (CH 2 COO – ) 3 ⋅ 2H 3 N + C(CH 2 OH) 3 , and 2,2'-(ethylenedioxy)bis(ethylammonium) nitrilotriacetate HN + (CH 2 COO – ) 3 ⋅ H 3 N + CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 N + H 3 . The molecular structures of 2-ammonioethanol nitrilotriacetate and bis{2-ammonio-2-(hydroxymethyl)propane-1,3-diol} nitrilotriacetate were determined. Nitrilotriacetic acid molecules in 2-ammonioethanol nitrilotriacetate are linked by O⋅⋅⋅H⋅⋅⋅O hydrogen bonds involving acid groups of adjacent molecules to form a polymer chain. On the contrary, nitrilotriacetic acid molecules in bis{2-ammonio-2-(hydroxymethyl)propane-1,3-diol} nitrilotriacetate do not form polymer chains. In the crystals of both compounds, adjacent molecules are linked by numerous O⋅⋅⋅H interactions to form infinite 3D frameworks.