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Type: Artigo de periódico
Title: Studies of the tautomeric equilibrium of 1,3-thiazolidine-2-thione: Theoretical and experimental approaches
Author: Abbehausen, C
de Paiva, REF
Formiga, ALB
Corbi, PP
Abstract: The tautomeric equilibrium of the thione/thiol forms of 1,3-thiazolidine-2-thione was studied by nuclear magnetic resonance, infrared and ultraviolet-visible spectroscopies. Density functional theory was used to support the experimental data and indicates the predominance of the thione tautomer in the solid state, being in agreement with previously reported crystallographic data. In solution, the tautomeric equilibrium was evaluated using H-1 NMR at different temperatures in four deuterated solvents acetonitrile, dimethylsulfoxide, chloroform and methanol. The equilibrium constants, K = (thiol)/(thione), and free Gibbs energies were obtained by integration of N bonded hydrogen signals at each temperature for each solvent, excluding methanol. The endothermic tautomerization is entropy-driven and the combined effect of solvent and temperature can be used to achieve almost 50% thiol concentrations in solution. The nature of the electronic transitions was investigated theoretically and the assignment of the bands was made using time-dependent DFT as well as the influence of solvent on the energy of the most important bands of the spectra. (C) 2012 Elsevier B.V. All rights reserved.
Subject: 1,3-Thiazolidine-2-thione
Tautomeric equilibrium
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.chemphys.2012.09.019
Date Issue: 2012
Appears in Collections:Unicamp - Artigos e Outros Documentos

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