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An Application of Hplc and Ion Chromatography To Study Intramolecular Charge Transfer in Polyhalogenated Systems

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Reaction of hydrated electrons with aromatics substituted with both bromine and chlorine results in the production of significant yields of chloride ion and the complementary bromine substituted phenyl radical. The total yields show that in all cases the reduction is essentially quantitative. For the dihalogenated benzenes and phenols the relative yields for C-Br and C-Cl bond rupture (0.86:0.14) reflect the relative rates for electron attachment at the Br and Cl positions, suggesting that there is little intramolecular charge transfer on the time scale of dissociation of the initial anion. In the case of dihalogenated benzoates about 40% of the reduction results in C-Cl bond rupture. In this case the added charge initially localized on the carboxyl group is transferred preferentially to the chlorine atom indicating that solvation of the intermediate radical anion must play an extremely important role in controlling the overall reduction process.

Affiliations: 1: Pacific Northwest Laboratories P.O. Box 999, P8-47 Richland, WA 99352 USA; 2: Radiation Laboratory and Department of Chemistry University of Notre Dame Notre Dame, IN 46556 USA


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