Collect. Czech. Chem. Commun. 1980, 45, 1269-1278

Hydrolysis kinetics and mechanism of acyl-1,3-diphenyltriazenes

Oldřich Pytela, Miroslav Večeřa and Pavel Vetešník

Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice


The hydrolysis rate constants of 3-(N-methylcarbamoyl)-1,3-diphenyltriazene (I), 3-(N-phenylcarbamoyl)-1,3-diphenyltriazene (II) and 3-acetyl-1,3-diphenyltriazene (III) have been determined in aqueous media within pH 0 to 14, Ho to 3 and H- to 15. The hydrolysis at pH < 2 and pH > 11 show specific acid and base catalysis, respectively, whereas within pH 2 to 11 non-catalyzed hydrolysis takes place. Activation parameters of the non-catalyzed and catalyzed hydrolysis have been determined. Quantum-chemical calculation of 3-carbamoyltriazene (IV) has been carried out by the MINDO/2 method. Hydrolysis mechanism of the studied compounds is suggested for the non-catalyzed, specific acid catalyzed and specific base catalyzed hydrolysis.