- P-ISSN 1225-0163
- E-ISSN 2288-8985
- P-ISSN1225-0163
- E-ISSN2288-8985
- SCOPUS, ESCI, KCI
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Electrochemical Studies on the Reaction of Superoxide Ion with Halocarbons in Aprotic Media
Analytical Science and Technology / Analytical Science and Technology, (P)1225-0163; (E)2288-8985
1995, v.8 no.4, pp.649-654
Jeon,
S., &
Choi,
Y.
(1995). Electrochemical Studies on the Reaction of Superoxide Ion with Halocarbons in Aprotic Media. , 8(4), 649-654.
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Abstract
The reactivity of superoxide ion(<TEX>$O{_2}^{-.}$</TEX>) with halogenated substrates is investigated by cyclic voltammetry and rotated ring-disk electrode method in aprotic solvents. The more positive the reduction potential of the substituted nitrile, the more facile is nucleophilic displacement by <TEX>$O{_2}^{-.}$</TEX>. The reaction rates of halogenonitriles with <TEX>$O{_2}^{-.}$</TEX> vary according to the leaving-group propensity of halide (Br>Cl>F). The relative reaction rates of other substituted nitriles are in the order of electron-withdrawing propensity of the substituent group (CN> <TEX>$C(O)NH_2$</TEX> >Ph, <TEX>$CH_2CN$</TEX>). The reaction of <TEX>$O{_2}^{-.}$</TEX> with dihalocarbons indicates that five-membered rings can be rapidly formed by the cyclization of substrate and <TEX>$O{_2}^{-.}$</TEX>, and the relative rates of cyclization depend on the number of methylenic carbons {<TEX>$Br(CH_2)_nBr$</TEX>, [n
- keywords
- Cyclic voltammetry, Rotating ring-disk electrode, Dioxygen reduction, Superoxide ion, Halogenonitriles, Dihalocarbons
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