KINETICS AND MECHANISM OF THE REACTIONS OF S-PHENYL DITHIOBENZOATES WITH BENZYLAMINES IN ACETONITRILE

Kinetic studies are carried out on the reaction of S-phenyl dithiobenz oates with benzylamines in acetonitrile at 30.0 degrees C. Small magni tude of rho(X) (beta(X)) as well as rho(Z) (beta(Z)) obtained suggests rate-limiting nucleophilic attack of the thiocarbonyl carbon. This is supported by the unusually small magnitude of rho(XY) and rho(YZ), al beit their signs do not agree with those expected. Moreover, the inver se secondary kinetic isotope effects (k(H)/k(D)<1.0) involving deutera ted benzylamine nucleophiles are also in line with the proposed mechan ism.