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HYDROLYSIS OF CHLOROSTILBENE OXIDE: I. HYDROLYSIS IN HOMOGENEOUS SYSTEMS
Citation:
Metwally, M. AND N. Wolfe. HYDROLYSIS OF CHLOROSTILBENE OXIDE: I. HYDROLYSIS IN HOMOGENEOUS SYSTEMS. U.S. Environmental Protection Agency, Washington, D.C., EPA/600/J-89/092 (NTIS PB90100868), 1989.
Description:
The hydrolysis kinetics of 4-chlorostilbene oxide (CSO) in buffered distilled water, in natural waters, and in sediment associated water are reported. he disappearance of CSO followed pseudo-first-order kinetics in buffered water over the experimental pH range of 3 to 11. elow pH 5, acid-catalyzed hydroIysis dominates, with a second-order rate constant of 11.3(+1.0) M-1min-1. bove pH 5, hydrolysis is independent of pH, with a rate constant of 1.02(+0.12) X 10-4min-1 at 25C. n natural waters, the hydrolysis rate constant of CSO had an average value of 0.59(+0.12) x 10-4 min-1. n sediment-associated water, the observed rate constant was 1.70(+0.05) X 10-4min-1. orption of CSO to the humic materials in natural waters and biotic effects in sediment-associated water appropriately explain the differences from sterile buffer solutions. uffer catalysis was observed, but on the other hand, a negative ionic strength effect was determined. he formation of diastereoisomers of 1-(4-chlorophenyl)-2-phenylethylene glycol as major products at both acidic and neutral pH values suggests that CSC undergoes acid-catalyzed as well as neutral hydroIysis reactions through an A-I carbonium ion mechanism. he rate constant for hydrolysis of CSO at pH 14 is only 7O% faster than the hydrolysis rate constant over the pH range of 5 to 11, which suggests that nucleophilic addition of hydroxide ion is not the main hydrolytic mechanism of CSO hydrolysis at high pH values.