The hydrolysis of benzonitrile has been carried out in sulphuric, perchloric, and hydrochloric acids over a wide range of acidities and temperatures. Analysis of these data by Zucker–Hammett, Bunnett, and Bunnett–Olsen criteria, and inverse solvent deuterium isotope effects are consistent with a mechanism involving equilibrium N-protonation, followed by rate-limiting attack of water on carbon.
C. J. Hyland and C. J. O'Connor, J. Chem. Soc., Perkin Trans. 2, 1973, 223 DOI: 10.1039/P29730000223
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