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Kinetic and equilibrium studies of σ-adduct formation and substitution in the reactions of sulphite ions with some alkyl and aryl ethers and thioethers

✍ Scribed by Michael R. Crampton; Anthony J. Holmes

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
72 KB
Volume
11
Category
Article
ISSN
0894-3230

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✦ Synopsis

Kinetic and equilibrium results are reported for the reactions of sulphite with the ethyl and phenyl ethers of 2,4,6-trinitrophenol and 2,4,6-trinitrothiophenol in 80/20 (v/v) water/DMSO. In each case 1:1 and 1:2 adducts are observed by reaction of sulphite at one or two unsubstituted ring positions respectively. In the case of the ethyl derivatives these adducts are long-lived; however, the phenyl derivatives rapidly yield 2,4,6-trinitrobenzenesulphonate, the substitution product. This difference is attributed to a change in the nature of the rate-determining step, from nucleophilic attack with the phenyl derivatives to leaving group departure with the alkyl derivatives.

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