A Comparative Nucleophilic Substitution at Carbon, Sulfur and Phosphorus Centers: (SN2@C), (SN2@S) and (SN2@P)

초록

The SN2@C involves the characteristic transition state [X?C(O)?Y]? reflected in the double-well potential energy surface (PES). Similarly, it was found to be the same in the SN2@S system except for the asymmetric nucleophilic attack. We considered symmetric and asymmetric nucleophilic reactions in our model systems. In the case of symmetric nucleophilic attack at the phosphorus (SN2@P), the reaction mechanism shows the double-well PES involving a transition state. In the case of asymmetric nucleophilic attack, two competing mechanisms were found: frontal or rear-side attack and the reaction mechanism depended on the conformation of the reactants.