Investigation of Acid-Catalyzed Hydrolysis of 4-Nitrophenyl-N-Acetyl-4-Methylbenzenesulfonimidate in Dioxane-Water Solutions

The hydrolysis of 4-nitrophenyl N-acetyl-4-methylbenzenesulfonimidate in aqueous 20%, 40%, and 60% (v/v) dioxane solutions of mineral acids was investigated. Rate maxima are observed for both perchloric and sulfuric acids since hydrolysis was studied over a wider range of acidity in 20%, and 40% (v/v) dioxane. Similarly, rate maxima are observed perchloric and hydrochloric acid in 60% (v/v) dioxane at high acid concentration. Analyses of the data by the Cox–Yates excess acidity method and temperature effects indicate hydrolysis by an A-2 mechanism.