Abstract
In an effort to determine the factors affecting penicillin stability in acid media, benzylpenicillin anilides were synthesized and subsequently hydrolyzed at 30° in a mixture of dimethylformamide and glycocoll buffer at a pH of 2.0. The log of the penicillin anilideβ-lactam ring amide bond hydrolysis velocity constant was found to vary linearly with the amine pK. The hydrolysis reaction was found to follow Hammet's equation. The value of the constantρ (−0.12) indicates insensitivity of the reaction to structural changes in the anilide molecule.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
E. P. Doyle, J. H. C. Nayler, and H. R. J. Waddington, J. Chem. Soc., 497 (1963).
E. P. Doyle, J. H. C. Nayler, H. Smith, et al., Nature191, 1091 (1961).
A. S. Khokhlov, E. M. Kleiner, and E. N. Druzhinina, Antibiotics, No. 6, 42 (1958).
E. F. Paparin and M. V. Solovskii, ibid., No. 11, 1000 (1965).
D. A. Johson, J. Am. Chem. Soc.,75, 3636 (1953).
A. Albert and E. P. Serjeant, Ionization Constants of Acids and Bases, London (1962).
The Analyst,74, 550 (1949).
Author information
Authors and Affiliations
Additional information
Translated from Khimiko-Farmatsevticheskii Zhurnal, No. 2, pp. 14–17, February, 1967.
Rights and permissions
About this article
Cite this article
Panarin, E.F., Solovskii, M.V. Acid hydrolysis of benzylpenicillin anilides. Pharm Chem J 1, 72–74 (1967). https://doi.org/10.1007/BF00768082
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00768082