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Mechanism of acid-catalysed decomposition of 3-alkyl-1,3-diphenyltriazenes by trichloroacetic acid in hexane
Pytela, Oldrich,Bednar, Roman,Kavalek, Jaromir
, p. 343 - 349 (2004)
Eight 3-alkyl-1,3-diaryltriazenes with methyl, ethyl, propyl, butyl, pentyl, isopropyl, sec-butyl and cyclohexyl substituents were synthesized and their rate constants of decomposition by trichloroacetic acid (0.01-0.25 mol dm-3) in hexane at 25°C were measured. The kinetic model and mechanism thereof were studied by modelling of the dependences of k obs on the concentration of trichloracetic acid. On the basis of this kinetic model and the interpretation of solvent effects, a reaction mechanism was suggested according to which the triazene reacts with monomer and obviously also opens the dimer of trichloroacetic acid in a single reaction step. At the same time, a non-reactive associate between the N1 nitrogen of triazene and two molecules of trichloroacetic acid is formed in the reaction mixture. The equilibrium and rate constants depend on the addition of trichloroacetic acid as the co-solvent. Copyright
