SECONDARY KINETIC ISOTOPE EFFECTS INVOLVING DEUTERATED NUCLEOPHILES

The secondary alpha-deuterium kinetic isotope effects (k(H)/k(D) involving deuterated nucleophiles are shown to be useful in determining variations of S(N)2 transition states with substituents in the nucleophile, substrate, and leaving group, and in providing experimental evidence in support of the mechanistic interpretation based on the sign and magnitude of cross-interaction constants p(ij).