Electrochemical synthesis of a new phosphonium betaine. Kinetic evaluation and antibacterial susceptibility

Cyclic voltammetry, controlled-potential coulometry, chronoamperometry, chronocoulometry and chronopotentiometry methods were used for the electrochemical study of 1-acetyl-4-(4-hydroxyphenyl)piperazine (APIP) in the presence of triphenylphosphine (TPP) as a nucleophile. The data show that electrochemically generated APIPox can serve as a Michael acceptor for nucleophilic attack by TPP to yield a new phosphonium betaine (APTP). In this work, we prepared a new product in good yield and purity by reaction of TPP with APIPox in an undivided cell equipped with carbon anode. Based on an EC mechanism, the observed homogeneous rate constant (kobs) of the Michael addition reaction of APIPox with TPP were estimated by comparing the experimental cyclic voltammograms with the digital simulated results. Furthermore, electrochemical oxidation of APIP has been studied both experimentally and theoretically to provide insight into the influence of natural charge and thermodynamic stability parameters on the type of chemical reaction which follows APIPox. In addition, the synthesized compound was evaluated for in vitro antibacterial. [Display omitted] •Electrochemical synthesis of a new phosphonium betaine.•Electrochemical study of 1-acetyl-4-(4-hydroxyphenyl)piperazine in the absence and presence of triphenylphosphine.•Antimicrobial activity of synthesized phosphonium betaine.•Computational studies on 1-acetyl-4-(4-hydroxyphenyl)piperazine and synthesized phosphonium betaine.•Mechanistic studies.