Structural Chemistry

, Volume 16, Issue 5, pp 507–514 | Cite as

A Theoretical Study on the Tautomerism of C-Carboxylic and Methoxycarbonyl Substituted Azoles

Article

Abstract

DFT calculations (B3LYP/6-31+G**) have been carried out on 106 tautomers and conformers of NH-azoles bearing CO2H and CO2CH3 groups. The following azoles systems have been studied: 2-substituted pyrroles, 2-substituted indoles, 2-substituted imidazoles, 2-substituted benzimidazoles, 4(5)-substituted imidazoles, 3(5)-substituted pyrazoles, 3-substituted indazoles (1H and 2H), 3,4(5)-substituted-1,2,3(5)-triazoles, 2,3(5)-substituted-1,2(3),4-triazoles, 4(5)-1,2,3,4(5)-tetrazoles. In the case of pyrazole, 3,5-disubstituted derivatives have also been computed, including four dimers.

Keywords

DFT calculations azoles tautomerism carboxylic acids esters 

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Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  1. 1.Instituto de Química Médica (C.S.I.C.)MadridSpain

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