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

Sason S. Shaik

doi:10.1002/ijch.198500121

Identity S_N2 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 journal › Article › peer-review

17 Scopus citations

Abstract

Reactivity trends in the identity S_N2 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 language	English
Pages (from-to)	367-374
Number of pages	8
Journal	Israel Journal of Chemistry
Volume	26
Issue number	4
DOIs	https://doi.org/10.1002/ijch.198500121
State	Published - 1985
Externally published	Yes

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10.1002/ijch.198500121

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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.",

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year = "1985",

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AB - 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.

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Identity S_N2 Reactions. The Relationship Between Transition State Geometry, Selectivity and the Mechanism of Solvent Action

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