α-Substituent effects and non-bonding electron interactions atthe SN2 transition state, an ab-initio study.

Daniel Kost; Kalman Aviram

doi:10.1016/S0040-4039(00)88374-4

α-Substituent effects and non-bonding electron interactions atthe S_N2 transition state, an ab-initio study.

Daniel Kost, Kalman Aviram

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

The trend in reactivity observed for methyl-, methylene-, and methoxymethyl-chlorides is rationalized in terms of turning on and off the four electron repulsion, at the transition state, between a lone pair on the substituent and a π orbital along the reaction coordinate.

Original language	English
Pages (from-to)	4157-4160
Number of pages	4
Journal	Tetrahedron Letters
Volume	23
Issue number	40
DOIs	https://doi.org/10.1016/S0040-4039(00)88374-4
State	Published - 1 Jan 1982

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "α-Substituent effects and non-bonding electron interactions atthe SN2 transition state, an ab-initio study.",

abstract = "The trend in reactivity observed for methyl-, methylene-, and methoxymethyl-chlorides is rationalized in terms of turning on and off the four electron repulsion, at the transition state, between a lone pair on the substituent and a π orbital along the reaction coordinate.",

author = "Daniel Kost and Kalman Aviram",

year = "1982",

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doi = "10.1016/S0040-4039(00)88374-4",

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T1 - α-Substituent effects and non-bonding electron interactions atthe SN2 transition state, an ab-initio study.

AU - Kost, Daniel

AU - Aviram, Kalman

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Y1 - 1982/1/1

N2 - The trend in reactivity observed for methyl-, methylene-, and methoxymethyl-chlorides is rationalized in terms of turning on and off the four electron repulsion, at the transition state, between a lone pair on the substituent and a π orbital along the reaction coordinate.

AB - The trend in reactivity observed for methyl-, methylene-, and methoxymethyl-chlorides is rationalized in terms of turning on and off the four electron repulsion, at the transition state, between a lone pair on the substituent and a π orbital along the reaction coordinate.

UR - http://www.scopus.com/inward/record.url?scp=0001360683&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)88374-4

DO - 10.1016/S0040-4039(00)88374-4

M3 - Article

AN - SCOPUS:0001360683

SN - 0040-4039

VL - 23

SP - 4157

EP - 4160

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

α-Substituent effects and non-bonding electron interactions atthe S_N2 transition state, an ab-initio study.

Abstract

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