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Dissociation energies of O–H bonds in alkylseleno- and alkyltelluro-substituted phenols

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Abstract

The O−H bond dissociation energy (D O−H) has been determined for eight alkylseleno-substituted phenols, one alkyltelluro-substituted phenol, and one alkyltelluro-substituted pyridinol. D O−H has been estimated by the intersecting-parabolas method from kinetic data using five reference compounds: α-tocopherol (D O−H = 330.0 kJ/mol), 3,5-di-tert-butyl-4-methoxyphenol (D O−H = 347.6 kJ/mol), 4-methylphenol (D O−H = 361.6 kJ/mol), 2,6-di-tert-butyl-4-methylthiophenol (D O−H = 336.3 kJ/mol), and 2,6-di-ter-tbutyl-4-methylphenol (D O−H = 338.0 kJ/mol). The following D O−H values (kJ/mol) have been obtained: 335.9 for 2,5,7,8-tetramethyl-2-phytyl-6-hydroxy-3,4-dihydro-2H-1-benzoselenopyran, 342.6 for 2-methyl-5-hydroxy-2,3-dihydrobenzoselenophene, 333.5 for 2,4,6,7-tetramethyl-5-hydroxy-2,3-dihydrobenzoselenophene, 339.4 for 2-tert-butyl-4-methoxy-6-octylselenophenol, 357.9 for dodecyl 3-(4-hydroxyphenyl) propyl selenide, 348.5 for dodecyl 3-(3,5-dimethyl-4-hydroxyphenyl)propyl selenide, 350.9 for dodecyl 3-(3-tert-butyl-4-hydroxyphenyl)propyl selenide, 338.0 for dodecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propyl selenide, 343.0 for 2,6-di-tert-butyl-4-(tellurobutyl-4′-phenoxy)phenol, and 338.8 for 6-octyltelluro-3-pyridinol. The stabilization energies of phenoxyl radicals containing R substituents (X = O, S, Se, Te) have been compared.

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  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia

    T. G. Denisova & E. T. Denisov

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  1. T. G. Denisova
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  2. E. T. Denisov
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Correspondence to E. T. Denisov.

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Original Russian Text © T.G. Denisova, E.T. Denisov, 2017, published in Kinetika i Kataliz, 2017, Vol. 58, No. 1, pp. 17–25.

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Denisova, T.G., Denisov, E.T. Dissociation energies of O–H bonds in alkylseleno- and alkyltelluro-substituted phenols. Kinet Catal 58, 15–23 (2017). https://doi.org/10.1134/S0023158417010013

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