Premium
Identity S N 2 Reactions. The Relationship Between Transition State Geometry, Selectivity and the Mechanism of Solvent Action
Author(s) -
Shaik Sason S.
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500121
Subject(s) - chemistry , reactivity (psychology) , selectivity , nucleophile , distortion (music) , identity (music) , alkyl , stereochemistry , solvent , geometry , computational chemistry , crystallography , catalysis , organic chemistry , physics , acoustics , medicine , amplifier , alternative medicine , mathematics , cmos , pathology , electronic engineering , engineering
Reactivity trends in the identity S N 2 reaction (X − + CH 3 X → XCH 3 + X − ) are discussed using the state correlation diagram model. The model projects that the activation process can be defined as a distortion effort to transfer a single electron from the nucleophile to the leaving group across the alkyl group (CH 3 ). Three domains of reactivity are discussed (a) the geometry of the transition state (looseness and tightness), (b) the intrinsic selectivity of substrates, and (c) the mechanism of solvent action. A link is drawn between these three domains, and a physical insight is provided.