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The structure of protonated 3-pyridyl-substituted 5-amino-1H-1,2,4-triazoles: an experimental and theoretical studyстатья
Информация о цитировании статьи получена из
Web of Science
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 26 января 2016 г.
- Авторы: Chernyshev V.M., Astakhov A.V., Rybakov V.B., Chernysheva A.V., Tarasova E.V.
- Журнал: Russian Chemical Bulletin
- Том: 63
- Номер: 12
- Год издания: 2015
- Издательство: Springer Nature
- Местоположение издательства: Switzerland
- Первая страница: 2591
- Последняя страница: 2598
- Аннотация: The molecular and crystal structures and tautomerism of protonated isomeric 3-pyridyl- substituted 5-amino-1H-1,2,4-triazoles were studied within the framework of density function- al theory and by X-ray analysis. According to B3LYP/6-311++G(2d,2p) calculations of six possible tautomeric forms A-F, tautomers A with the N-protonated pyridine moiety are predominant in the gas phase. 5-Amino-4H-1-onium compounds (tautomers D) of higher polarity are next in stability; their relative energies decrease as follows: 3-pyridin-4-yl-, 3-pyridin-3-yl-, and 3-pyridin-2-yl-5-amino-4H-1,2,4-triazol-1-onium cation. A comparison of experimental C-13 NMR spectra of tautomers A and D with their NMR spectra calculated by the GIAO method showed that both tautomeric forms can coexist in comparable amounts in DMSO solutions. Tautomers A and D were detected by X-ray analysis in crystals of 5-amino-3-(pyrid- in-2-yl)-1H-1,2,4-triazolium salts.
- Добавил в систему: Рыбаков Виктор Борисович