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The tautomerism of 1,2,3-triazole, 3(5)-methylpyrazole and their cations

✍ Scribed by Javier Catalán; Marta Sánchez-Cabezudo; José Luis G. De Paz; José Elguero; Robert W. Taft; Frederick Anvia

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
656 KB
Volume
10
Category
Article
ISSN
0192-8651

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✦ Synopsis

The annular tautomerism of 1,2,3-triazole and 3(5)-methylpyrazole is discussed by means of a combination of theoretical calculations and experimental (ICR) gas-phase basicities and acidities. In the gas phase 1,2,3-triazole exists as the ZH-tautomer, whereas both tautomers of 3(5)-methylpyrazole are of similar energy. The solvent effects on these prototropic equilibria are discussed taking into account solvent properties as polarity/polarizability, acidity, and basicity. In nonhydrogen bonding solvents, the difference in dipole moments between both tautomers plays a role that has usually been underestimated.

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