Abstract
To examine the stability of penicillin and its derivatives in an alkaline medium the hydrolysis of substituted anilides of benzylpenicillin was studied at pH 9.1 and temperatures of 25, 30, and 40°. The velocity constants of the reaction and the activation energy of the process were calculated; hydrolysis of the amide bond of theβ-lactam ring of anilides of benzylpenicillin under these conditions was shown to be a pseudomonomolecular reaction. A satisfactory correlation was found between the logarithms of the velocity constants of the reaction and the pK of the amine. Hammett's equation is applicable to this process. The low absolute values ofρ=0.33 indicate that the reaction is only slightly sensitive to structural changes in the anilide molecule.
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Translated from Khimiko-Farmatsevticheskii Zhurnal, No. 2, pp. 17–21, February, 1967.
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Panarin, E.F., Solovskii, M.V. Study of alkaline hydrolysis of anilides of benzylpenicillin. Pharm Chem J 1, 75–77 (1967). https://doi.org/10.1007/BF00768083
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DOI: https://doi.org/10.1007/BF00768083