Rate-acidity correlation for the base-promoted dehydrochlorination of DDT in methanol. Evidence for E1cB elimination | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

2147592

Reference Type

Journal Article

Title

Rate-acidity correlation for the base-promoted dehydrochlorination of DDT in methanol. Evidence for E1cB elimination

Author(s)

Mclennan, DJ; Wong, RJ

Year

1972

Is Peer Reviewed?

Journal

Tetrahedron
ISSN: 0040-4020

Report Number

HAPAB/72/02559

Volume

Lett

Issue

Lett.

Page Numbers

2891-2894

Abstract

HAPAB Recently published work by Streitweiser has shown that a Bronsted-type correlation exists between log kT2 the rate constants for second-order detritiation of tritiated indene and fluorene-type hydrocarbons in MeO SUP- eOH at 45 DEG , and the hydrocarbon pKa values relative to cesium cyclohexylamide in cyclohexylamine. To support a previously proposed mechanism of the dehydrochlorination of DDT via the ''irreversible'' carbanion or E1cB mechanism, these values pertaining to DDT were calculated, and were shown to lie on the Streitweiser Bronsted plot. There was some discrepancy between isotope effects and the Bronsted beta value for the DDT/p-RC(SUB)6H(SUB)4O SUP- reaction series, but these have been noted in other cases. It was concluded that beta is the less reliable criterion of transition state structure. 1972