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Effect of donor and acceptor properties of solvents on the kinetics of photoreduction of sterically hindered о-benzoquinones

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Abstract

Effect of the solvent nature on the kinetics of photoreduction of 3,6-di-tert-butyl-1,2-benzoquinone and its six derivatives in the presence of N,N-dimethylaniline and 4-(N,N-dimethylamino)benzaldehyde has been investigated. It has been found that for the о-quinone—amine pair, for which the free energy change of electron transfer is ΔG e > +0.11 eV, the rate constant of о-quinone photoreduction k H decreases proportionally to the increase in the acceptor number of the solvent. For the о-quinone—amine pair with ΔG e < +0.11 eV, the k H value decreases proportionally to the increase in the donor number of the solvent. It has been established that the enhancement of the electron-acceptor properties of the solvent leads to the emergence of kinetic isotope effect for the reactant pairs of 3,6-di-tert-butyl-1,2-benzoquinone and 4,5-dimethoxy-3,6-di-tert-butyl-1,2-benzoquinone with N,N-di-methylaniline (ΔG e = +0.11 and +0.22 eV, respectively).

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Authors and Affiliations

  1. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, ul. Tropinina 49, Nizhny Novgorod, 603950, Russia

    M. P. Shurygina, S. A. Chesnokov & G. A. Abakumov

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  1. M. P. Shurygina
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  2. S. A. Chesnokov
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  3. G. A. Abakumov
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Correspondence to S. A. Chesnokov.

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Original Russian Text © M.P. Shurygina, S.A. Chesnokov, G.A. Abakumov, 2016, published in Khimiya Vysokikh Energii, 2016, Vol. 50, No. 5, pp. 376—381.

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Shurygina, M.P., Chesnokov, S.A. & Abakumov, G.A. Effect of donor and acceptor properties of solvents on the kinetics of photoreduction of sterically hindered о-benzoquinones. High Energy Chem 50, 356–361 (2016). https://doi.org/10.1134/S0018143916050131

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  • DOI: https://doi.org/10.1134/S0018143916050131

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