A comparison of ring-chain tautomerism in heterocycles derived from 2-aminobenzenesulfonamide and anthranilamide |
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Authors: | Olga A Maloshitskaya Valery V Alekseyev Kalevi Pihlaja |
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Institution: | a Department of Chemistry, Structural Chemistry Group, University of Turku, FI-20014 Turku, Finland b Russian Military Medical Academy, 194044 St. Petersburg, Russian Federation |
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Abstract: | A number of anthranilamide and 2-aminobenzenesulfonamide derivatives with aromatic aldehydes and 1,3-dicarbonyl compounds were synthesized. Substituted benzaldehyde derivatives of neither aminoamides showed tautomerism in solutions. Reaction products of 2-aminobenzenesulfonamide with p-substituted benzoylacetic aldehydes and p-substituted benzoylacetones undergo ring-chain tautomerism with a good linear correlation between the ring-chain equilibrium constants (log K, where K=ring]/chain]) and the Hammett-Brown σ+ parameters of the aromatic substituents. The equilibrium constant was measured for the reaction products of 2-aminobenzenesulfonamide with unsubstituted benzoylacetaldehyde at several temperatures which enabled the enthalpy and entropy of this reaction to be evaluated. |
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Keywords: | Ring-chain tautomerism Anthranylamide 2-Aminobenzenesulfonamide 1 3-Dicarbonyl compounds |
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