Journal of the Chemical Society. Perkin transactions II p. 423 - 428 (1984)
Update date:2022-08-11
Topics:
Kohnstam, George
Petch, W. Andrew
Williams, D. Lyn H.
Acidity-rate profiles have been established for the rearrangement of N-phenylhydroxylamine and its derivatives in aqueous sulphuric acid and also in D2SO4-D2O.The results, particularly the change in the magnitude of the kinetic solvent isotope effect on increasing the acidity, are consistent only with a reaction mechanism involving unimolecular decomposition of the O-protonated species.N-Ethyl substitution has only a very small effect on the overall rate of reaction, whereas the rate constant was increased by ca. 100 by 4-Me substitution.The substituent effects argue against the involvement of a nitrenium ion intermediate but rather suggest that the intermediate is better represented by an imine structure with the positive charge at the 4-position in the aromatic ring.
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