Kinetic dependence of the aqueous reaction of N-(hydroxymethyl)benzamide derivatives upon addition of electron-withdrawing groups.
[figure: see text] The rate constants for the hydronium ion, hydroxide, and water-catalyzed breakdown of N-(hydroxymethyl)benzamide (1), 4-chloro-N-(hydroxymethyl)benzamide (2), and 2,4-dichloro-N-(hydroxymethyl)benzamide (3) in H2O, at 25 degrees C, I = 1.0 (KCl), have been determined. The reactions of 1, 2, and 3 were found to be specific acid and specific base catalyzed with a first-order dependence on hydronium and hydroxide ions. At higher hydroxide concentrations, the reactions were found to be pH independent for each compound studied.
Tenn
W J
WJ
Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA.
French
N L
NL
Nagorski
R W
RW
D001549:Benzamides / Q000737:chemistry* / Q000493:pharmacokinetics; D002384:Catalysis; D005557:Formaldehyde / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D014867:Water / Q000737:chemistry
C430484:2,4-dichloro-N-(hydroxymethyl)benzamide; D001549:Benzamides; D014867:Water; C050284:4-chloro-N-(hydroxymethyl)benzamide; D005557:Formaldehyde; C037309:N-hydroxymethylbenzamide