Collect. Czech. Chem. Commun. 1990, 55, 147-155

Solvent effects on kinetics and mechanism of acid-catalyzed decomposition of 1,3-bis(4-methylphenyl)triazene I. Reactions in alcohols

Taťjana Nevěčnáa, Oldřich Pytelab, Miroslav Ludwigb and Jaromír Kaválekb

a Department of Inorganic and Physical Chemistry, Palacký University, 771 46 Olomouc
b Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice


The effect of protic solvents (methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, cyclohexanol) has been studied on the kinetics and mechanism of acid-catalyzed decomposition of 1,3-bis(4-methylphenyl)triazene, using trichloroacetic acid as the acid catalyst. Both the non-dissociated acid and the proton have been found to be catalytically active. The mechanism of splitting of the triazene substrate with the non-dissociated acid involves the general acid catalysis. Comparison of the catalytic rate constants of the two acid catalysts and effect of solvents on these values indicate that the general acid catalysis probably also operates in the reaction of the substrate with proton.