O. Maloshitskaya, J. Sinkkonen, V. V. Alekseyev
Jul 25, 2005
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
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.