Russian Journal of General Chemistry p. 461 - 479 (2008)
Update date:2022-07-29
Topics:
Buzykin
Mironova
Nabiullin
Azancheev
Avvakumova
Rizvanov
Gubaidullin
Litvinov
Syakaev
New complexing agents, potentially tautomeric 3-(2-hydroxyethylsulfanyl)- 1H-1,2,4-triazole, its 5-methyl-and 5-phenyl-substituted analogs, and some their salts, were synthesized, and their structure was discussed on the basis of the 1H and 13C NMR, IR, and mass spectra, X-ray diffraction data, and published data. In keeping with the rule formulated previously for N-unsubstituted 1,2,4-triazoles having dissimilar substituents, the synthesized compounds were found to exist as 3-(2-hydroxyethylsulfanyl)-5-R-1H-1,2,4- triazole tautomers (3-RA-5-RD-1H-1,2,4-triazoly). They are protonated at the nitrogen atom in position 4 of the triazole ring. The 1H and 13C NMR spectra of these compounds in trifluoroacetic acid suggest the presence of two forms due to equilibrium between the neutral and protonated species. Analysis of the crystallographic data for the triazolium salts and published data showed preference of the 1H,4H-1,2,4-triazolium tautomer.
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