Electrochemical oxidation of acetaminophen in the presence of Methyl- Meldrum’s acid: Experimental and Theoretical Studies

Acetaminophen (1,4-acetamidophenol) is a popular medicine, and electrochemical behavior of it has been studied in aqueous and non-aqueous solvents [1]. The electrochemical oxidation of acetaminophen in the presence of different nucleophiles has been investigated [2, 3]. In this work electrochemical oxidation of acetaminophen in the presence of Methyl-Meldrum’s acid (MMA) has been studied both experimentally and theoretically. The experimental results were obtained using cyclic voltammetry and controlled-potential coulometry, and also the computational data was obtained by the use of density functional theory (DFT). The theoretical results were calculated at (B3LYP) level of theory and 6-311G(p,d) basis set. Acetaminophen oxidized to its pbenzoquinoneimine (1ox) via two-electron, two-proton process, and the produced 1ox is unstable and reacts with MMA as a nucleophile. According to the voltammetry and coulometry study and by the use of the computational data, a mechanism was presented for the electrochemical oxidation of acetaminophen in the presence of Methyl-Meldrum’s acid (MMA). Also using computational study, a mechanism was estimated for the electrochemical oxidation of 1,2-acetamidophenol in the presence of Methyl-Meldrum’s acid (MMA).