Abstract
The hydrolysis of benzene, p-toluene,
p-bromobenzene, and p-nitrobenzene sulphonyl chlorides in 10-60 wt. %
water-dioxan and water-acetone has been shown to follow an SN2 mechanism. The reaction does not show acid catalysis
or any " salt " effect. Hammett?s equation does not describe fully
the effects of substituents on the reaction rate.
For solutions in which water has the same
molarity, aqueous acetone gives lower rates than aqueous dioxan when the
molarity of water is high but higher rates when the molarity of water is low.
Change in the water content of the solvent produces only small changes in the
enthalpy of activation except in solutions of low dielectric constant. The
reduction in rate as solutions become less aqueous is mainly determined by the
entropy of activation becoming more strongly negative.
Cited by
40 articles.
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