Conclusions
-
1.
The kinetic principles of the hydrolysis of metanitroacetanilide and metanitroformanilide in aqueous solutions of potassium hydroxide were studied by a spectrophotometric method.
-
2.
The process of hydrolysis is irreversible, and the change in the concentration of the anilides with time is well described by a first-order equation.
-
3.
The mechanism of ionization and the mechanism of the limiting step of hydrolysis of the investigated anilides in aqueous solutions of potassium hydroxide were established according to the dependence of the effective rate constant on the alkalinity of the medium b0 and the activity of water\(a_{H_2 O} \).
-
4.
Metanitroformanilide and metanitroacetanilide exist in aqueous solutions of potassium hydroxide in three equilibrium forms: nonionized (B), singly ionized (BOH−), and doubly ionized (BOO=).
-
5.
The limiting step in the process of hydrolysis is the decomposition of the complex of the doubly ionized form of the anilide and two water molecules (BOO=·2H2O).
Similar content being viewed by others
Literature cited
S. S. Biechler and R. W. Taft, J. Amer. Chem. Soc.,79, 4927 (1957).
M. I. Vinnik and Y. V. Moiseyev, Tetrahedron,19, 1441 (1963).
M. I. Vinnik, Yu. V. Moiseev, and L. V. Palagina, Dokl. Akad. Nauk SSSR,143, 1127 (1962).
A. T. Babayan, M. I. Vinnik, A. Kh. Pochikyan, and P. S. Chobanyan, Izv. Akad. Nauk SSSR, Ser. Khim., 295 (1971).
R. A. Robinson and R. M. Stokes, Trans. Faraday Soc.,45, 612 (1949); E. Shibata, J. Kobayashi, and S. Fukinawa, J. Chem. Soc., Japan,52, 404 (1931).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 39–45, January, 1972.
Rights and permissions
About this article
Cite this article
Vinnik, M.I., Pochikyan, A.K. Kinetics and mechanism of the hydrolysis of metanitroacetanilide and metanitroformanilide in aqueous solutions of KOH. Russ Chem Bull 21, 34–38 (1972). https://doi.org/10.1007/BF00855651
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00855651