Identity SN2 Reactions. The Relationship Between Transition State Geometry, Selectivity and the Mechanism of Solvent Action

Sason S. Shaik*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Reactivity trends in the identity SN2 reaction (X + CH3X → XCH3 + 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 (CH3). 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.

Original languageEnglish
Pages (from-to)367-374
Number of pages8
JournalIsrael Journal of Chemistry
Volume26
Issue number4
DOIs
StatePublished - 1985
Externally publishedYes

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