Tautomerism and basicity of carboxylic acid guanyl hydrazides (acylaminoguanidines)

Авторы: Astakhov A.V., Tarasova E.V., Chernysheva A.V., Rybakov V.B., Starikova Z.A., Chernyshev V.M.
Журнал: Russian Chemical Bulletin, Int. Ed
Том: 70
Номер: 8
Год издания: 2021
Первая страница: 1509
Последняя страница: 1522
DOI: 10.1007/s11172-021-3246-8
Аннотация: The acid-base properties, structures, and tautomerism of protonated and free forms ofcarboxylic acid guanyl hydrazides (acylaminoguanidines) were studied using experimental andtheoretical methods. According to the experimental data, guanyl hydrazides are relatively strong bases (pKa 8.1—8.9 in water at 25 С) in spite of the presence of the electron-withdrawing carbonyl group in their molecules. The results of studying by NMR spectroscopy, X-ray diff raction 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.
Добавил в систему: Рыбаков Виктор Борисович

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