Nucleophilic reactivities of Schiff bases

摘要

The nucleophile-specific parameters N and s_N, as defined by the linear free energy relationship log k = s_N(N+E) (J. Am. Chem. Soc. 2001, 123, 9500 - 9512), were determined for five imines 1a-e by studying the kinetics of their reactions with benzhydrylium ions in dichloromethane solution at 20 °C. These parameters allowed us to include representative Schiff bases into our comprehensive nucleophilicity scale and compare their reactivities with those of other N-nucleophiles.