Abstract
Abstract The effect of solvents on the position of keto- cis - trans -enolic equilibrium of a series of 3-alkylacetylacetones has been studied. The bromometric and IR evidence for 1% solutions gives a sound qualitative picture but owing to insufficient dilution does not elucidate pertinent quantitative regularities. The latter was achieved by studying UV spectra with dilution down to 10 −4 m/l. As a measure of concentration of tautomeric forms integral densities of absorption bands assigned to cis - and trans -enolic forms were used. The data obtained led to the conclusion that cis -enolization of 3-alkylacetylacetones follows Meyer's rule whereas trans -enolization is independent of the nature of the solvent. The overall enolization is expressed as K T = EL + E 1 . The specificity of β-dicarbonyl compounds as a particular chemical type in terms of the Bronsted-Izmailov theory is discussed.
Published Version
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