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

Victor Glezer, Batsheva Harris, Nelly Tal, Berta Iosefzon, Ovadia Lev*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

179 Scopus citations

Abstract

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.

Original languageAmerican English
Pages (from-to)1938-1948
Number of pages11
JournalWater Research
Volume33
Issue number8
DOIs
StatePublished - Jun 1999

Bibliographical note

Funding Information:
This research was supported by the Avicennia initiative of the European Community; German Federal Ministry of Education, Science, Research and Technology (BMFT) and the Israeli Ministry of Science (MOS) and U.S. EPA.

Keywords

  • Chlorination products
  • Haloacetonitriles
  • Hydrolysis
  • LFER

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