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Paper | Special issue | Vol 82, No. 1, 2010, pp.479-489
Published online, 22nd June, 2010
DOI: 10.3987/COM-10-S(E)21
Relative Stabilities of 1- and 2-Substituted 1,2,3-Triazoles

Alan R. Katritzky,* Ana-Maria Buciumas, Ekaterina Todadze, Munawar Ali Munawar, and Levan Khelashvili

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.

Abstract

N-(α-Aminoalkyl)-1,2,3-triazoles are potentially tautomeric between the 1- and 2-substituted forms. They exist in solution predominantly as 2-isomers as shown by 1H and 13C NMR; electron attracting substituents on the amino nitrogen increase the proportion of the 1-isomer in the equilibrium mixture.