Hadi Beiginejad - Faculty of Science, Malayer University, P. O. Box ۶۵۷۱۹, Malayer, Iran

Electrochemical oxidation of some 4-phenylurazole species (1-5) has been investigated theoretically to provide insight into the influence of some factors on the ring cleavage reaction rate. It was reported that the electrochemically produced form (1ox-5ox) are unstable and participate in ring cleavage reaction, and also observed homogeneous rate constants of ring cleavage reaction of them were determined using digital simulation technique. The effect of charge of reaction site (C1) and N1–C1 bond order (Wiberg Bond Indices, WBIs) on the hydrolysis rate constant were studied. All calculations were performed using Density Functional Theory (DFT) B3LYP level of theory and 6-311G (p,d) basis set. Results of the present research indicate that the rate of ring cleavage increases upon increasing positive charge of C1, and also the rate of ring cleavage decreases upon increasing WBIs of N1–C1.

4-phenylurazole species, ring cleavage, WBIs, positive charge