Hydrolysis of haloacetonitriles: Linear free energy relationship. Kinetics and products

  • Glezer V
  • Harris B
  • Tal N
 et al. 
  • 21


    Mendeley users who have this article in their library.
  • 115


    Citations of this article.


The hydrolysis rates of mono-, di- and trihaloacetonitriles were studied in aqueous buffer solutions at different pH. The stability of haloacetonitriles decreases and the hydrolysis rate increases with increasing pH and number of halogen atoms in the molecule. The monochloroacetonitriles are the most stable and are also less affected by pH-changes, while the trihaloacetonitriles are the least stable and most sensitive to pH changes. The stability of haloacetonitriles also increases by substitution of chlorine atoms with bromine atoms. The hydrolysis rates in different buffer solutions follow first order kinetics with a minimum hydrolysis rate at intermediate pH. Thus, haloacetonitriles have to be preserved in weakly acid solutions between sampling and analysis. The corresponding haloacetamides are formed during hydrolysis and in basic solutions they can hydrolyze further to give haloacetic acids. Linear free energy relationship can be used for prediction of degradation of haloacetonitriles during hydrolysis in water solutions.

Author-supplied keywords

  • Chlorination products
  • Haloacetonitriles
  • Hydrolysis
  • LFER

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document


Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free