Trichloroethylene oxide is produced from oxidative metabolism of trichloroethylene (TCE), which causes inactivation of cytochrome P450, proteins and DNA.To better understand the hydrolysis mechanism, a systematic ab initio investigation of the water-assisted decomposition of TCE-oxide as a function of the number of water molecules building up the solvation shell is presented. The reactions are accelerated substantially as the reaction system involves additional explicit coordination of water molecules that act as a bridge to activate the release of a Cl- leaving group. The predominant pathway and the rate-determining step are found. Rate constant is in reasonable agreement with experiments. Certain intermediates are supposed to be responsible for the reaction with nucleophiles in the body that could give a hint for risk assessment of this kind of water pollutant. The mechanism for the water-assisted decomposition and probable implications for the reaction of these chlorinated epoxide compounds in natural environment are briefly discussed.

Theoretical study of the mechanism of the aqueous decomposition of trichloroethylene oxide

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.