SELF-PROTONATION OF ELECTROGENERATED CARBANIONS - COMPETITION BETWEENELECTRODE REDUCTION AND CHEMICAL DECAY OF THE CONJUGATE BASE OF THE SUBSTRATE

The problem of the electrochemical detection of the conjugate base of the parent compound arising in the self-protonation of electrogenerate d carbanions has been addressed. In particular, the case in which the conjugate base decays according to a first-order reaction in competiti on with its electrode reduction has been theoretically analyzed for th e voltammetric method. The outcome of the calculations has been succes sfully compared with experimental data obtained for a representative c ase such as the reduction of self-protonating 2-bromo-2,N-dimethylprop anamide in NN'-dimethylformamide.