Quantitative structure-electrochemistry relationships of α, β-unsaturated ketones

Abstract

The half-wave potential ( E 1 2 ) of 26 substituted α,β-unsaturated ketones in non-aqueous acetonitrile were used in Hammett type quantitative structure-activity relationship (QSAR) analysis. A linear relationship between E 1 2 and the electronic substituent constant, σ x and reaction constant gr R was revealed for 17 substituted chalcones. Linear regression equations were calculated using only the sum of σ x, para + σ x, meta of all substituents. It was found that the production of the substituted 1,2-oxaphosphol-4-en in the redox reaction of the α,β-unsaturated ketones and trialkyl phosphite can be predicted from the E 1 2 values of the α,β-unsaturated ketones measured in nonprotic solvent. The E 1 2 values also give a linear correlation with the conversions of the starting ketones.