Kinetics of Proton Transfer from 2-Nitro-4-X-phenylacetonitriles to Piperidine and Morpholine in Aqueous Me2SO. Solvent and Substituent Effects on Intrinsic Rate …

CF Bernasconi, PJ Wenzel

Index: Bernasconi, Claude F.; Wenzel, Philip J. Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11446 - 11453

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Citation Number: 29

Abstract

Rate constants () for the deprotonation of 2-nitro-4-X-phenylacetonitrile, 2-X (X= NO2, SO2CH3, CN, CF3, Br, and Cl) by piperidine and morpholine and for the reverse reaction () have been determined in 90% Me2SO-10% water, 50% Me2SO-50% water, and water (X= NO2, SO2CH3, CN only). Brønsted βB values (dlog/dp), Brønsted αCH values (dlog/dlog), and intrinsic rate constants (log ko= log (k 1/q) for p-p+ log (p/q)= 0) were calculated from ...