Application of the NT Solvent Nucleophilicity Scale to Attack at Sulfur: Solvolyses of Benzenesulfonyl Chlorides

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Title:Application of the NT Solvent Nucleophilicity Scale to Attack at Sulfur: Solvolyses of Benzenesulfonyl Chlorides
Creators:
Kevill, Dennis N.
D'Souza, Malcolm J.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 11, pp. 1790-1796
Uncontrolled Keywords:Reaction kinetics, Extended Grunwald-Winstein equation, Solvent nucleophilicity, Solvolysis, Benzenesulfonyl chlorides

Abstract

The specific rates of solvolysis of benzenesulfonyl chloride and three 4-substituted derivatives can be very well correlated using the extended Grunwald-Winstein equation, with incorporation of <i>N</i><sub>T</sub> solvent nucleophilicity and <i>Y</i><sub>Cl</sub> solvent ionizing power values. In two instances, it was shown that almost identical correlations were obtained after the incorporation of methyl groups into the 2- and 6-positions of the benzene ring. No evidence was found for a dissociative (S<sub>N</sub>1) mechanism or for a duality of mechanism. All of the results can be rationalized in terms of a concerted bimolecular displacement (S<sub>N</sub>2) mechanism, involving attack by solvent at sulfur. <p>

Title:Application of the NT Solvent Nucleophilicity Scale to Attack at Sulfur: Solvolyses of Benzenesulfonyl Chlorides
Creators:
Kevill, Dennis N.
D'Souza, Malcolm J.
Uncontrolled Keywords:Reaction kinetics, Extended Grunwald-Winstein equation, Solvent nucleophilicity, Solvolysis, Benzenesulfonyl chlorides
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:11
Page Range:pp. 1790-1796
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991790UNSPECIFIED
ID Code:1596
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:11

Citation

Kevill, Dennis N.; D'Souza, Malcolm J. (1999) Application of the NT Solvent Nucleophilicity Scale to Attack at Sulfur: Solvolyses of Benzenesulfonyl Chlorides. Collection of Czechoslovak Chemical Communications, 64 (11). pp. 1790-1796. ISSN 0010-0765

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