Experimental and theoretical study of hydrolysis for some oxidized urazoles

Abstract

In this work electrochemical oxidation of some urazole derivatives (1–6) was studied both experimentally and theoretically. The results indicate that the urazoles are converted to oxidized forms (1ox-6ox) via two electron process. The produced species (1ox-6ox) are unstable and participate in hydrolysis reaction, and ring cleavage happens after electrochemical process. Depending on the substituent that is connected to the urazol ring, the rates of the hydrolysis are different. Because the charge of reaction site and bond order of C1-N1 bond are effective on the hydrolysis rate, using computational study, the effects of the both parameters on the hydrolysis rate were analyzed. It was found that various substituents by affecting on the both parameters change the hydrolysis rate. After drawing diagrams of charge of reaction site and bond order of C1-N1 bonds versus hydrolysis rate, it was shown that there are significant relationship between these parameters and hydrolysis rate. Finally these results were used to estimation of hydrolysis rate of some other urazoles (7-10) without conducting laboratory research.