Fenton's reagent. IV. Structure and reactivity relations in the reactions of hydroxyl radicals and the redox reactions of radicals
Reactivities of a variety of alcohols, ethers, and amides toward hydroxyl radicals have been examined. Results are in encouraging agreement with radiation chemistry results. Reactivities of different C- H bonds have been dissected from the data and indicate that the hydroxyl radical is a strongly electrophilic species, so that electron supply is more important than C--H bond strength in determining reactivity. Comparison with gas-phase data shows similar reactivity patterns, but considerably faster reactions in H/sub 2/O. Radicals alpha to --OH, --OR, and amide N are readily oxidized by Fe/sup 3+/; tert-alkyl radicals are oxidized with more difficulty and allyl radicals hardly at all. In contrast, radicals RC (OH)CCl/sub 3/ are reduced by Fe/sup 2+/. Results are consistent with a fast oxidation of easily oxidized radicals by Fe/sup 3+/ via electron transfer, and a slower more general oxidation of radicals by Cu/sup 2+/ via a RCu(III) intermediate. (auth)
- Research Organization:
- Univ. of Utah, Salt Lake City
- Sponsoring Organization:
- USDOE
- NSA Number:
- NSA-29-012589
- OSTI ID:
- 4370461
- Journal Information:
- J. Amer. Chem. Soc., v. 96, no. 1, pp. 133-139, Other Information: Orig. Receipt Date: 30-JUN-74
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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