Kinetics and mechanistic study of oxidation of acetoacetanilide through free radical pathway by an oxidant diperiodatocuprate(III) in aqueous alkaline medium

The oxidation of acetoacetanilide by Cu(III) complex in an aqueous alkaline medium was investigated spectrophotometrically at different temperature range 288–318 K. The study was conducted with a fixed ionic strength of 0.30 mole dm−3. The stoichiometric ratio between diperiodatocuprate(III) and acetoacetanilide was found to be 2:2. To understand the reaction pathway, a free radical participation was obtained by radical interruption studies. The proposed mechanism involves the formation of intermediate species, which subsequently decomposes in successive steps to yield the reaction product as a dimer 3,6-dioxo-N1,N8-diphenyloctanediamide. Reaction mechanism confirms that the monoperiodatocuprate(III) act as active oxidizing species in the reaction. The reaction products were identified using spot tests, infrared (IR) spectroscopy, and LC–MS analysis. The equilibrium constants associated with the proposed mechanism, along with the rate constant and activation parameters for the rate-determining step, were evaluated and discussed.