Geometrical and stereochemical factors in metal-promoted amide hydrolysis

JT Groves, R Rife, R Chambers Jr

Index: Groves,J.T.; Chambers,R.R. Journal of the American Chemical Society, 1984 , vol. 106, p. 630

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Citation Number: 83

Abstract

Abstract: The importance of the precise geometric orientation of a metal in metal-promoted amide hydrolysis has been demonstrated. Large rate enhancements (103-106) at neutral pH were found in zinc and copper complexes in which the metal is forced to lie above the plane of an amide. For this study, lactams 1-[(6-(dimethylamino) methyl)-2-pyridyl) methyl] hexahydro-1, 4-diazepin-5-one (1) and 1-[(6-((bis (carboxymethyl) amino) methyl)-2- ...