Acid- and base-catalyzed hydrolysis of chloroacetamide herbicides.

Journal Article (Journal Article)

Despite the prevalence of chloroacetamides as herbicides, little is known about the rates or products of acid- or base-catalyzed hydrolysis of these compounds. Mechanisms of acid-catalyzed reactions may parallel those catalyzed by (hydr)oxide minerals, while base-catalyzed processes have as important counterparts reactions with environmental nucleophiles (such as reduced sulfur species). The current study systematically investigates how the structure of nine chloroacetamides affects their reactivity in 2 N NaOH, 2 N HCl, or 6 N HCl at 25 or 85 degrees C. Base-catalyzed hydrolysis proceeds either through an intermolecular SN2 reaction to hydroxy-substituted derivatives or (in a few cases) through amide cleavage, while both amide and ether group cleavages are observed under acidic conditions. Our results reveal that subtle differences in chloroacetamide structure [notably the type of (alkoxy)alkyl substituent] can dramatically influence reactivity and reaction mechanism. Hydroxy-substituted, morpholinone, and secondary aniline derivatives were identified upon reaction for several years in deionized water at circumneutral pH.

Full Text

Duke Authors

Cited Authors

  • Carlson, DL; Than, KD; Roberts, AL

Published Date

  • June 28, 2006

Published In

Volume / Issue

  • 54 / 13

Start / End Page

  • 4740 - 4750

PubMed ID

  • 16787023

International Standard Serial Number (ISSN)

  • 0021-8561

Digital Object Identifier (DOI)

  • 10.1021/jf0530704


  • eng

Conference Location

  • United States