Identity S N 2 Reactions. The Relationship Between Transition State Geometry, Selectivity and the Mechanism of Solvent Action | Zendy

Shaik Sason S. | Zendy

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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.

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