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- W1982137071 abstract "We have studied the enol-imine→keto-amine tautomeric equilibrium of N-salicylidene-p-X-aniline compounds with X = Me, OMe, NMe2 as electron donor substituents and X = COMe, CN and NO2 as electron acceptor substituents. The equilibrium constants (K°tau) and standard thermodynamic properties ΔG°tau, ΔH°tau and ΔS°tau were measured and calculated in methanol solution at various temperatures, by means of excitation fluorescence spectroscopy. We have analyzed the p-phenylaniline substitution effect on K°tau and the thermodynamic properties through the Hammett parameters σ. We have performed molecular orbital calculations at the semiempirical AM1 and ab initio HF/3-21G levels to interpret the experimental results, explicitly including the solute–solvent interaction through the formation of an intermolecular hydrogen bond between the salicylidene and methanol molecules. These computational results show a good correlation with the experimental values. An interpretation of the experimental values of TΔS°, based on changes in the molecular structure produced in the enol-imine→keto-amine tautomeric reaction, is proposed." @default.
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- W1982137071 date "2001-01-01" @default.
- W1982137071 modified "2023-09-27" @default.
- W1982137071 title "A study of the tautomers of N-salicylidene-p-X-aniline compounds in methanol" @default.
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- W1982137071 doi "https://doi.org/10.1039/b101041g" @default.
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