Abstract
The temperature dependence of rate constants for the pseudo-first-order hydrolysis of 2-methylbenzenesulfonyl chloride, 1,5-naphthalenedisulfonyl chloride, and 4-acetamidobenzenesulfonyl chloride in water-2-propanol mixtures is studied in the i-PrOH mole fraction range x2 = 0−0.10. The concentration dependences of the enthalpy of activation and the entropy contribution (ϑ = 100(−TΔS≠)/(ΔG≠, %) for the hydrolyses of all sulfonyl chlorides are nonmonotonic, depending on the sulfonyl chloride structure and the degree of complementarity of the hydration complexes to the solvent structure. The sulfonyl chlorides are hydrolyzed via two pathways: one of them involves a water dimer as a bifunctional catalyst along with a water molecule as a nucleophile, and the other involves an alcohol hydrate.
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