A. C. Knipe, J. Lound-Keast, N. Sridhar
1984
Citations
0
Influential Citations
6
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
The intramolecular rearrangement of 2-(p-nitrophenoxy)ethylamine to 2-(p-nitroanilino)ethanol occurs by a general-base-catalysed process in aqueous alkali; the attainment of a base-independent rate limit at high base concentration can be attributed to rate-determining formation of a spiro-Meisenheimer intermediate. The reaction kinetics can be interpreted in terms of the specific-base–general-acid-catalysed mechanism or by invoking rate-determining deprotonation of the spiro-Meisenheimer intermediate; the latter inerpretation provides the best explanation of the coefficient β= 0.20–0.35 and curvilinear form of the Bronsted correlation and is consistent with the kinetics of reactions of analogous polynitro systems reported by Bernasconi.