Pulse radiolysis studies of aminobenzenesulfonates: Formation of cation radicals

David Behar; Bracha Behar

doi:10.1021/j100172a078

Pulse radiolysis studies of aminobenzenesulfonates: Formation of cation radicals

David Behar^*, Bracha Behar

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

Sulfanilic acid and anilinedisulfonic acids (ADS) react with OH radicals (k = 8.2 × 10⁹ and 5.9 × 10⁹ M^-1 s^-1) to form the corresponding OH adducts. In acid solutions the adducts react with protons to yield cation radicals (k = 5.3 × 10⁸ and 8.7 × 10⁸ M^-1 s^-1). N₃ oxidizes sulfanilic acid directly to the cation radical by an electron-transfer reaction at a diffusion-controlled rate constant, k = 6.5 × 10⁹ M^-1 s^-1, while the rate of oxidation of ADS by N₃ is only 7.6 × 10⁷ M^-1 s^-1. SO₄^- on the other hand oxidizes ADS to the cation radical at a rate of 1.8 × 10⁹ M^-1 s^-1. Both cation radicals deprotonate to the anilino-type radicals in acid-base equilibria. The pK_a of deprotonation of the sulfanilic cation radical is 5.8 ± 0.05 and that of the ADS cation radical is 4.3 ± 0.05.

Original language	English
Pages (from-to)	7552-7556
Number of pages	5
Journal	Journal of Physical Chemistry
Volume	95
Issue number	19
DOIs	https://doi.org/10.1021/j100172a078
State	Published - 1991
Externally published	Yes

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title = "Pulse radiolysis studies of aminobenzenesulfonates: Formation of cation radicals",

abstract = "Sulfanilic acid and anilinedisulfonic acids (ADS) react with OH radicals (k = 8.2 × 109 and 5.9 × 109 M-1 s-1) to form the corresponding OH adducts. In acid solutions the adducts react with protons to yield cation radicals (k = 5.3 × 108 and 8.7 × 108 M-1 s-1). N3 oxidizes sulfanilic acid directly to the cation radical by an electron-transfer reaction at a diffusion-controlled rate constant, k = 6.5 × 109 M-1 s-1, while the rate of oxidation of ADS by N3 is only 7.6 × 107 M-1 s-1. SO4- on the other hand oxidizes ADS to the cation radical at a rate of 1.8 × 109 M-1 s-1. Both cation radicals deprotonate to the anilino-type radicals in acid-base equilibria. The pKa of deprotonation of the sulfanilic cation radical is 5.8 ± 0.05 and that of the ADS cation radical is 4.3 ± 0.05.",

author = "David Behar and Bracha Behar",

year = "1991",

doi = "10.1021/j100172a078",

language = "אנגלית",

volume = "95",

pages = "7552--7556",

journal = "Journal of Physical Chemistry",

issn = "0022-3654",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Pulse radiolysis studies of aminobenzenesulfonates

T2 - Formation of cation radicals

AU - Behar, David

AU - Behar, Bracha

PY - 1991

Y1 - 1991

N2 - Sulfanilic acid and anilinedisulfonic acids (ADS) react with OH radicals (k = 8.2 × 109 and 5.9 × 109 M-1 s-1) to form the corresponding OH adducts. In acid solutions the adducts react with protons to yield cation radicals (k = 5.3 × 108 and 8.7 × 108 M-1 s-1). N3 oxidizes sulfanilic acid directly to the cation radical by an electron-transfer reaction at a diffusion-controlled rate constant, k = 6.5 × 109 M-1 s-1, while the rate of oxidation of ADS by N3 is only 7.6 × 107 M-1 s-1. SO4- on the other hand oxidizes ADS to the cation radical at a rate of 1.8 × 109 M-1 s-1. Both cation radicals deprotonate to the anilino-type radicals in acid-base equilibria. The pKa of deprotonation of the sulfanilic cation radical is 5.8 ± 0.05 and that of the ADS cation radical is 4.3 ± 0.05.

AB - Sulfanilic acid and anilinedisulfonic acids (ADS) react with OH radicals (k = 8.2 × 109 and 5.9 × 109 M-1 s-1) to form the corresponding OH adducts. In acid solutions the adducts react with protons to yield cation radicals (k = 5.3 × 108 and 8.7 × 108 M-1 s-1). N3 oxidizes sulfanilic acid directly to the cation radical by an electron-transfer reaction at a diffusion-controlled rate constant, k = 6.5 × 109 M-1 s-1, while the rate of oxidation of ADS by N3 is only 7.6 × 107 M-1 s-1. SO4- on the other hand oxidizes ADS to the cation radical at a rate of 1.8 × 109 M-1 s-1. Both cation radicals deprotonate to the anilino-type radicals in acid-base equilibria. The pKa of deprotonation of the sulfanilic cation radical is 5.8 ± 0.05 and that of the ADS cation radical is 4.3 ± 0.05.

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DO - 10.1021/j100172a078

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AN - SCOPUS:0013552927

SN - 0022-3654

VL - 95

SP - 7552

EP - 7556

JO - Journal of Physical Chemistry

JF - Journal of Physical Chemistry

IS - 19

ER -

Pulse radiolysis studies of aminobenzenesulfonates: Formation of cation radicals

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