Carbanion reactivity; kinetics of the reactions of benzyl cyanide anions with aromatic nitro-compounds

Abstract

Rate and equilibrium measurements are reported for the reactions in methanol of carbanions derived from 12 ring-substituted benzyl cyanides with 1,3,5-trinitrobenzene to give σ-adducts. Some data for reaction of the carbanions with 4-nitrobenzofuroxan were also measured. With increasing carbanion reactivity, rate constants approach a limit of just below 10⁹ dm³ mol^–1 s^–1. Intrinsic reactivities of carbanions in σ-adduct forming reactions and in proton transfer reactions are compared.