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On the Tautomeric Structure of 5-hydroxy- and 5-mercapto-1H-1,2,3-triazoles: −13C NMR analysis

✍ Scribed by Gerrit L'abbé; Pieter Delbeke; Gonda van Essche; Ingrid Luyten; Karin Vercauteren; Suzanne Toppet

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
176 KB
Volume
99
Category
Article
ISSN
0037-9646

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✦ Synopsis

Dedicated to Professor G. Smets on the occasion of his 75th birthday

The title compounds have been analyzed by 13C NMR spectroscopy and compared with the N-3 methyl and O/S alkyl derivatives. The mesoionic structures 2a,b are rejected in favour of la,b on the basis of the 2Jc5 = CH coupling constants and the chemical shifts. Incremental substituent effects for triazoles are discussed.

5-Hydroxy-l-' and 5-mercapto-1 H-l,2,3-triazole~~-~~ have been prepared on several occasions and are usually drawn as the aromatic structures la,b, although the mesoionic structures 2a,b are also conceivable.

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