Hydrolysis of p-nitrotrifluoroacetanilide catalyzed by water and imidazole |
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Authors: | Makoto Komiyama Myron L Bender |
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Institution: | Division of Biochemistry, Department of Chemistry, Northwestern University, Evanston, Illinois 60201 USA |
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Abstract: | The hydrolyses of p-nitrotrifluoroacetanilide catalyzed by water and imidazole were examined at 70°C. The pH-rate constant profile of the hydrolysis in H2O was examined in the pH range 0.0–11.4. The hydrolysis was independent of pH in the region from pH 1.0 to 4.5, presumably a water-catalyzed reaction. The rate constant and the D2O solvent isotope effect for this reaction were 1.0 × 10?4 sec?1 and 3.7, respectively. Both natural imidazole and imidazolium cation catalyzed hydrolysis. The rate constant of the hydrolysis catalyzed by neutral imidazole was determined to be 5.4 × 10?3M?1 sec?1 and the D2O solvent isotope effect was 1.8. |
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