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The tautomerism of 1,2,3‐triazole, 3(5)‐methylpyrazole and their cations
Author(s) -
Catalán Javier,
SánchezCabezudo Marta,
De Paz José Luis G.,
Elguero José,
Taft Robert W.,
Anvia Frederick
Publication year - 1989
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540100318
Subject(s) - tautomer , chemistry , polarizability , solvent , gas phase , computational chemistry , 1,2,4 triazole , dipole , solvent effects , triazole , medicinal chemistry , organic chemistry , molecule
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.