Aminequinone-hydroxylquinoneimine tautomeric equilibrium revisited: molecular modeling study of the tautomeric equilibrium and substituent effects in 4-(4-R-phenylamino)naphthalene-1,2-diones |
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Authors: | Thaís P Fragoso José Walkimar de Mesquita Carneiro Maria D Vargas |
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Institution: | 1. Departamento de Química Inorganica, Instituto de Química, Universidade Federal Fluminense, Outeiro de S?o Jo?o Batista, s/n, 24020-141, Niterói, RJ, Brazil
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Abstract: | Semi-empirical (AM1 and PM3) and DFT (B3LYP/6-31G(d)) calculations were employed to study the tautomeric equilibrium between
the aminequinone A and hydroxylquinoneimine B forms of 4-(4-R-phenylamino)naphthalene-1,2-diones. Substituent effects on the tautomeric equilibrium as well as on geometric
and electronic parameters were also determined. In the gas phase the hydroxylquinoneimine B form is the most stable, whereas in water the aminequinone A form becomes more stable. The substituents do not modify the relative energies of the two tautomers. These results are in
accordance with experimental data reported in the literature. |
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