The tautomerism of 1,2,3-triazole, 3(5)-methylpyrazole and their cations |
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Authors: | Javier Cataln Marta Snchez-Cabezudo Jos Luis G De Paz Jos Elguero Robert W Taft Frederick Anvia |
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Institution: | Javier Catalán,Marta Sánchez-Cabezudo,José Luis G. De Paz,José Elguero,Robert W. Taft,Frederick Anvia |
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Abstract: | 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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