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Tautomerism and basicity of carboxylic acid guanyl hydrazides (acylaminoguanidines)

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Abstract

The acid-base properties, structures, and tautomerism of protonated and free forms of carboxylic acid guanyl hydrazides (acylaminoguanidines) were studied using experimental and theoretical methods. According to the experimental data, guanyl hydrazides are relatively strong bases (pKa 8.1-8.9 in water at 25 °C) in spite of the presence of the electron-withdrawing carbonyl group in their molecules. The results of studying by NMR spectroscopy, X-ray diffraction analysis, and DFT calculations show that in polar media free guanyl hydrazides predominantly exist as zwitterionic tautomers (inner salts) with positive charge localization on the protonated guanidine moiety and negative charge localization on the deprotonated amide group.

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  1. M. I. Platov South-Russian State Polytechnic University, 132 ul. Prosveshcheniya, 346428, Novocherkassk, Russian Federation

    A. V. Astakhov, E. V. Tarasova, A. V. Chernysheva & V. M. Chernyshev

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. B. Rybakov

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Z. A. Starikova

Authors
  1. A. V. Astakhov
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  2. E. V. Tarasova
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  3. A. V. Chernysheva
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  4. V. B. Rybakov
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  5. Z. A. Starikova
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  6. V. M. Chernyshev
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Corresponding author

Correspondence to V. M. Chernyshev.

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The authors are grateful to the Center for Collective Use “Nanotechnologies” at the M. I. Platov South-Russian State Polytechnic University and the Department of Structural Investigation at the N. D. Zelinsky Institute of Organic Chemistry (Russian Academy of Sciences) for analytical experiments.

This work was financially supported by the Russian Science Foundation (Project No. 19-73-10100).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

† Deceased.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1509–1522, August, 2021.

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Astakhov, A.V., Tarasova, E.V., Chernysheva, A.V. et al. Tautomerism and basicity of carboxylic acid guanyl hydrazides (acylaminoguanidines). Russ Chem Bull 70, 1509–1522 (2021). https://doi.org/10.1007/s11172-021-3246-8

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  • DOI: https://doi.org/10.1007/s11172-021-3246-8

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