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Effects of indole and imidazole derivatives on the radiation- and peroxide-induced transformations of ethanol

  • Radiation Chemistry
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Abstract

The interaction of indole, imidazole, and their derivatives with α-hydroxyethyl radicals has been studied by the radiation and peroxide initiation of free-radical processes. The enthalpies of H-atom addition to the multiple bonds of the test compounds, which characterize their oxidation properties, have been calculated within the framework of the density functional theory. The set of experimental and theoretically calculated data indicate that serotonin or β-carboline alkaloids (harmine, harman, and harmaline) inhibit the formation of 2,3-butanediol—the main radiolysis product of deaerated ethanol—mainly due to reduction and addition or the oxidation of α-hydroxyethyl radicals, respectively. Enhancement of oxidation properties in the above order of β-carboline alkaloids has been observed. Pyrrole, indole, melatonin, imidazole, 1-methylimidazole, and 2-mercapto-1-methylimidazole exhibit low reactivity toward α-hydroxyethyl radicals.

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Authors and Affiliations

  1. Belarussian State University, pr. Nezavisimosti 4, Minsk, 220030, Belarus

    S. D. Brinkevich, R. L. Sverdlov & O. I. Shadyro

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  1. S. D. Brinkevich
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  2. R. L. Sverdlov
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  3. O. I. Shadyro
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Correspondence to O. I. Shadyro.

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Original Russian Text © S.D. Brinkevich, R.L. Sverdlov, O.I. Shadyro, 2013, published in Khimiya Vysokikh Energii, 2013, Vol. 47, No. 1, pp. 19–27.

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Brinkevich, S.D., Sverdlov, R.L. & Shadyro, O.I. Effects of indole and imidazole derivatives on the radiation- and peroxide-induced transformations of ethanol. High Energy Chem 47, 12–20 (2013). https://doi.org/10.1134/S0018143913010037

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  • DOI: https://doi.org/10.1134/S0018143913010037

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