The mechanism of acyl sulphonate reactions. Part II. Solvolyses of a series of 4- and 5-substituted 2-sulphobenzoic anhydrides in hydroxylic solvents
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 454-456
- https://doi.org/10.1039/j29710000454
Abstract
Rate constants have been determined for the solvolyses of 5-chloro-2-sulphobenzoic anhydride in five alcohols, 4-bromo-, 4-chloro-, 4-methyl-, and 4-nitro-2-sulphobenzoic anhydride in four alcohols, and 4-iodo-2-sulphobenzoic anhydride in three alcohols, each alcohol containing 6·67% ether. Rate constants for the hydrolysis and deuteriolysis of the 4-methyl compound in 90% dioxan were also obtained. Hammett ρ values and solvent effects are interpreted as indicating a synchronous mechanism with a transition state in which bond forming has proceeded further than bond breaking.Keywords
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