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

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Abstract

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+(CH2COO–)2(CH2COOH) ⋅ H3N+CH2CH2OH]n, bis{2-ammonio-2-(hydroxymethyl)propane-1,3-diol} nitrilotriacetate HN+(CH2COO–)3 ⋅ 2H3N+C(CH2 OH)3, and 2,2'-(ethylenedioxy)bis(ethylammonium) nitrilotriacetate HN+(CH2COO–)3 ⋅ H3N+CH2CH2OCH2CH2OCH2CH2N+H3. 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.

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Funding

The study was performed within the framework of the state assignment (subject no. 45.8 “Chemistry of Functional Materials,” registration no. 0094-2016-0012) using equipment of the Analytical Center of the Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences and was financially supported by the Federal Target Program “Research and Development in Priority Areas of the Science and Technology Complex of Russia for 2014—2020” (unique project identifier RFMEFI62120X0040). The work was financially supported by the Presidium of the Russian Academy of Sciences (program no. 35 “Scientific Foundations for Design of New Functional Materials”). The single-crystal X-ray diffraction studies were carried out within the framework of the state assignment (subject no. 44.2, registration no. AAAA-A16-116122110053-1).

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Authors and Affiliations

  1. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 603950, Nizhny Novgorod, Russia

    R. V. Rumyantcev, N. V. Zolotareva, O. V. Novikova, B. I. Petrov, N. M. Lazarev & V. V. Semenov

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  1. R. V. Rumyantcev
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  2. N. V. Zolotareva
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  3. O. V. Novikova
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  5. N. M. Lazarev
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  6. V. V. Semenov
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Correspondence to V. V. Semenov.

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Translated by T. Safonova

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Rumyantcev, R.V., Zolotareva, N.V., Novikova, O.V. et al. Complexes of Nitrilotriacetic Acid with Amines. Molecular Structures of 2-Ammonioethanol Nitrilotriacetate and Bis{2-Ammonio-2-(Hydroxymethyl)propane-1,3-Diol} Nitrilotriacetate. Crystallogr. Rep. 66, 441–447 (2021). https://doi.org/10.1134/S1063774521030214

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