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1 2001

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Mechanism of Ring Opening Reaction of 4-Benzylidene-2-methyl-5-oxazolone. Part I. Reaction with n-Butylamine

Betłakowska B., Banecki B., Łankiewicz L., Wiczk W.

Polish Journal of Chemistry

2001

Vol. 75, nr 3

401-410

The reaction between 4-benzylidene-2-methyl-5-oxazolone (Ox, c = 5.25 _ 10-5 M) with n-butylamine (nBuA, c = 0.026 to 1.66 M) in acetonitrile was studied by UV-Vis spectroscopy using steady-state and stopped-flow apparatus. The amine to Ox molar ratio higher than 500 allows to apply pseudo-first order approximation, whose rate constants depend on amine concentration according to a parabolic equation: kobs = 4.63 _ 0.02 _ CnBuA 2 , indicating a complex reaction mechanism. On the other hand, singular value decomposition (SVD) analysis, as well as global analysis of the data obtained from stopped-flow measurements support a simple A B reaction model. Nonlinear dependence of the pseudo- first order rate constant on amine concentration can be explained, assuming that the oxazolone ring opening reaction by n-butylamine in acetonitrile proceeds as parallel reactions: A + B C and A+2B C. Based on our experimental results and theoretical calculations of the oxazolone ring opening reaction, a mechanism of the reaction between 4-benzylidene-2-methyl-5-oxazolone and n-butylamine is proposed.