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 2H‐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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Catalán et al. (1989) studied this question.
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