Abstract
The dependence of the hydrolysis of 1-methyl-2-benzoylmethylenehexahydroazepine on the pH of the solution was studied. It is shown that the dependence of the observed rate constant (kobs) on the pH is represented by a bell-shaped curve. At pH 3–6, kobs depends on the acetic acid concentration in an acetate buffer with the same pH value. The addition of potassium acetate to a 0.1 N HCl solution gives rise to a statistically reliable increase in kobs. It was shown by means of a model compound that the O-protonated form of the enamino ketones is resistant to hydrolysis. A mechanism for the hydrolysis of 1-methyl-2-benzoylmethylenehexahydroazepine in which the rate-determining step at pH 0–6 is C protonation is proposed.
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See [1] for communication 6.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1678–1682, December, 1979.
Original article submitted February 7, 1979.
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Kiselev, S.S., Polievktov, M.K. & Granik, V.G. Enamines. 7. kinetics of the hydrolysis of 1-methyl-2-benzoylmethylenehexahydroazepine in acidic media. Chem Heterocycl Compd 15, 1352–1356 (1979). https://doi.org/10.1007/BF00514742
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DOI: https://doi.org/10.1007/BF00514742