Journal of the American Chemical Society

Metal ion promoted hydroxide ion and water catalyzed hydrolysis of amides. Effects of the acyl group and the leaving group

TH Fife, R Bembi

Index: Fife, Thomas H.; Bembi, Ramesh Journal of the American Chemical Society, 1993 , vol. 115, # 24 p. 11358 - 11363

Full Text: HTML

Citation Number: 42

Abstract

Abstract: The hydrolysis of anilide derivatives of N-methyl-4-nitroaniline in HzO is hydroxide ion catalyzed; plots of log kow vs pH are linear with slopes of 1.0 at pH> 8. When there is a chelating functional group in the acyl portion of the molecule (1, lO-phenanthrolinyl or 6- carboxypicolinoyl) and in the presence of saturating concentrations of Cu2+, Co2+, or Zn2+, hydroxide ion catalyzed reactions are observed at pH> 4 (rate enhancements range from ...