Conclusions
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1.
The available data on the acid hydrolysis of benzamide, N-methylbenzamide, and N,N-dimethyl-benzamide can be quantitatively described on the basis of the following assumptions: a) the spectrally observed amide ionization results in complex formation through H3O+ ion addition to the carbonyl group of the amide; b) hydrolysis in salt-free solution follows two different paths, the one through the complex resulting from addition of an H3O+ ion, solvated with at least one water molecule, to the nitrogen atom of the un-ionized amide form, the other through monomolecular breakdown into the products resulting from BH3O+ hydrolysis.
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2.
Equilibrium constants for BH3O+ complexing, and rate constants for each of the hydrolysis paths, have been evaluated for various temperatures.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 799–807, April, 1978.
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Vinnik, M.I. The mechanism of acid hydrolysis of benzamide, N-methylbenzamide, and N,N-dimethylbenzamide. Russ Chem Bull 27, 689–695 (1978). https://doi.org/10.1007/BF00925285
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DOI: https://doi.org/10.1007/BF00925285