A Unified Framework for Understanding Nucleophilicity and Protophilicity in the S_N 2/E2 Competition.

ABSTRACT: The concepts of nucleophilicity and protophilicity are fundamental and ubiquitous in chemistry. A case in point is bimolecular nucleophilic substitution (S_N 2) and base-induced elimination (E2). A Lewis base acting as a strong nucleophile is needed for S_N 2 reactions, whereas a Lewis base acting as a strong protophile (i.e., base) is required for E2 reactions. A complicating factor is, however, the fact that a good nucleophile is often a strong protophile. Nevertheless, a sound, physical model that explains, in a transparent manner, when an electron-rich Lewis base acts as a protophile or a nucleophile, which is not just phenomenological, is currently lacking in the literature. To address this fundamental question, the potential energy surfaces of the S_N 2

SUBMITTER: Vermeeren P 

PROVIDER: S-EPMC7756690 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature