The kinetic isotope effect of hydrogen for sulfonation with sulfur trioxide has been determined at 25.0° in a competitive study, using hexadeuterated and ordinary benzene, askH/kD= 1.14 ± 0.06. Hydrogen exchange between benzene and benzenesulfonic acid is relativelys slow under these conditions and does not interfere with the determination of the isotope effect. Diphenylsulfone was found as a by‐product in the sulfonation reaction. The kinetic isotope effect for the sulfonylation of benzene at 25.0° was found to bekH/kD= 0.86 ± 0.06. It is proposed that the hydrogen exchange between benzene and anhydrous benzenesulfonic acid proceeds according to a SE‐2 type of mechanism.
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Cerfontain et al. (1964) studied this question.
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