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Substituent and Solvent Effects on the Tautomerism of 1-Phenylazo-2-Naphthol: A Computational Study
1, 2 , 3 , 4 , 1
1  Institut für Chemie, Karl-Franzens-Universität Graz, Heinrichstrasse 28, 8010 Graz, Austria
2  Department of Chemistry, Federal Urdu University of Arts, Science & Technology, Gulshan-e-Iqbal, Science Campus, Karachi, Sindh, Pakistan
3  Department of Crystallography and Crystal Chemistry, University of Lodz, Pomorska 149/153, 90-236 Lodz, Poland
4  Institute of Organic Chemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria

Abstract: The tautomerism between enol and inone forms of 1-phenylazo-2-naphthol is discussed in this work. The density functional theory (DFT) method is used at the level of B3LYP/6-31+G(d,p) for computations and it showed good agreement with the experimental data qualitatively. Generally quinone forms (of studied compounds) are more stable than naphthol forms. Electron attracting groups move the equilibrium also towards quinone form while releasing groups move the equilibrium to the naphthol form. The polarity of solvents does not have significant effect on the equilibrium.
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