Arylperoxyl radicals. Formation, absorption spectra, and reactivity in aqueous alcohol solutions

Z. B. Alfassi; G. I. Khaikin; P. Neta

doi:10.1021/j100001a041

Arylperoxyl radicals. Formation, absorption spectra, and reactivity in aqueous alcohol solutions

Z. B. Alfassi, G. I. Khaikin, P. Neta

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34 Scopus citations

Abstract

Aryl radicals (phenyl, 4-biphenylyl, 2-naphthyl, 1-naphthyl, and 9-phenanthryl) were produced by the reaction of the corresponding aryl bromide with solvated electrons and reacted rapidly with oxygen to produce the arylperoxyl radicals. These radicals exhibit optical absorptions in the visible range, with 2_max at 470, 550, 575, 650, and 700 nm, respectively. Arylperoxyl radicals react with 2,2′-azinobis(3-ethylbenzothiazoiine-6-sulfonate ion) (ABTS), chlorpromazine, and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox C) by one-electron oxidation. The rate constants k for these reactions, determined from the rate of formation of the one-electron oxidation products as a function of substrate concentration, vary between 4 × 10⁶ and 2 ×10⁹ L mol^-1 s^-1 and increase in the order phenyl-, 4-biphenyl-, 2-naphthyl-, 1-naphthyl-, and 9-phenanthrylperoxyl, the same order as the absorption peaks of these radicals. Good correlation was found between log k and the energy of the absorption peak.

Original language	English
Pages (from-to)	265-268
Number of pages	4
Journal	Journal of Physical Chemistry
Volume	99
Issue number	1
DOIs	https://doi.org/10.1021/j100001a041
State	Published - 1 Jan 1995
Externally published	Yes

ASJC Scopus subject areas

General Engineering
Physical and Theoretical Chemistry

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title = "Arylperoxyl radicals. Formation, absorption spectra, and reactivity in aqueous alcohol solutions",

abstract = "Aryl radicals (phenyl, 4-biphenylyl, 2-naphthyl, 1-naphthyl, and 9-phenanthryl) were produced by the reaction of the corresponding aryl bromide with solvated electrons and reacted rapidly with oxygen to produce the arylperoxyl radicals. These radicals exhibit optical absorptions in the visible range, with 2max at 470, 550, 575, 650, and 700 nm, respectively. Arylperoxyl radicals react with 2,2′-azinobis(3-ethylbenzothiazoiine-6-sulfonate ion) (ABTS), chlorpromazine, and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox C) by one-electron oxidation. The rate constants k for these reactions, determined from the rate of formation of the one-electron oxidation products as a function of substrate concentration, vary between 4 × 106 and 2 ×109 L mol-1 s-1 and increase in the order phenyl-, 4-biphenyl-, 2-naphthyl-, 1-naphthyl-, and 9-phenanthrylperoxyl, the same order as the absorption peaks of these radicals. Good correlation was found between log k and the energy of the absorption peak.",

author = "Alfassi, {Z. B.} and Khaikin, {G. I.} and P. Neta",

year = "1995",

month = jan,

day = "1",

doi = "10.1021/j100001a041",

language = "English",

volume = "99",

pages = "265--268",

journal = "Journal of Physical Chemistry",

issn = "0022-3654",

publisher = "American Chemical Society",

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T1 - Arylperoxyl radicals. Formation, absorption spectra, and reactivity in aqueous alcohol solutions

AU - Alfassi, Z. B.

AU - Khaikin, G. I.

AU - Neta, P.

PY - 1995/1/1

Y1 - 1995/1/1

N2 - Aryl radicals (phenyl, 4-biphenylyl, 2-naphthyl, 1-naphthyl, and 9-phenanthryl) were produced by the reaction of the corresponding aryl bromide with solvated electrons and reacted rapidly with oxygen to produce the arylperoxyl radicals. These radicals exhibit optical absorptions in the visible range, with 2max at 470, 550, 575, 650, and 700 nm, respectively. Arylperoxyl radicals react with 2,2′-azinobis(3-ethylbenzothiazoiine-6-sulfonate ion) (ABTS), chlorpromazine, and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox C) by one-electron oxidation. The rate constants k for these reactions, determined from the rate of formation of the one-electron oxidation products as a function of substrate concentration, vary between 4 × 106 and 2 ×109 L mol-1 s-1 and increase in the order phenyl-, 4-biphenyl-, 2-naphthyl-, 1-naphthyl-, and 9-phenanthrylperoxyl, the same order as the absorption peaks of these radicals. Good correlation was found between log k and the energy of the absorption peak.

AB - Aryl radicals (phenyl, 4-biphenylyl, 2-naphthyl, 1-naphthyl, and 9-phenanthryl) were produced by the reaction of the corresponding aryl bromide with solvated electrons and reacted rapidly with oxygen to produce the arylperoxyl radicals. These radicals exhibit optical absorptions in the visible range, with 2max at 470, 550, 575, 650, and 700 nm, respectively. Arylperoxyl radicals react with 2,2′-azinobis(3-ethylbenzothiazoiine-6-sulfonate ion) (ABTS), chlorpromazine, and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox C) by one-electron oxidation. The rate constants k for these reactions, determined from the rate of formation of the one-electron oxidation products as a function of substrate concentration, vary between 4 × 106 and 2 ×109 L mol-1 s-1 and increase in the order phenyl-, 4-biphenyl-, 2-naphthyl-, 1-naphthyl-, and 9-phenanthrylperoxyl, the same order as the absorption peaks of these radicals. Good correlation was found between log k and the energy of the absorption peak.

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U2 - 10.1021/j100001a041

DO - 10.1021/j100001a041

M3 - Article

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SN - 0022-3654

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EP - 268

JO - Journal of Physical Chemistry

JF - Journal of Physical Chemistry

IS - 1

ER -

Arylperoxyl radicals. Formation, absorption spectra, and reactivity in aqueous alcohol solutions

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