Kinetics and equilibrium in the ammonolysis of substituted phthalimides

…, NE Seaman, JM Duff, RE Branston

Index: McClelland, Robert A.; Seaman, N. Esther; Duff, James M.; Branston, R. E. Canadian Journal of Chemistry, 1985 , vol. 63, p. 121 - 128

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Citation Number: 13

Abstract

Kinetic studies are reported for the base hydrolysis to phthalamic acid anions (H) and ammonolysis to phthalamides (A) for seven phthalimides (P): 1, unsubstituted; 2, 4-NO2; 3, 4- Cl; 4, 4-t Bu; 5, 3-NO2; 6, 3-Me; 7, 3-Me3Si. The hydrolysis kinetics require two mechanisms, one which is first order in neutral imide and first order in hydroxide ion, and a second, which is important only in quite concentrated NaOH, which is first order in neutral phthalimide ...

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