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Kinetic analysis of the reactivity of peroxyl radicals in chain oxidation of unsaturated compounds

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Abstract

The array of rate constants (323 K) for the addition of peroxyl radicals of different structures to the π-bonds of unsaturated compounds was obtained. These data were analyzed using a combination of correlation and quantum chemical methods. The prospects of using Denisov’s parabolic model are shown in comparison with classical linear correlations. It is noted that QSPR models using quantum chemical and structural descriptors can also be used to estimate the reactivity of reacting particles in this elementary act. The obtained kinetic information can be the basis for elucidating the detailed mechanism of oxidation of biologically significant molecules.

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Notes

  1. When chains are initiated by the reaction of molecular oxygen with a substrate molecule (O2 + RH), the chain initiation rate in autooxidation mode W0 is used instead of Wi [22, 25]

  2. \(\lg k = \lg k_{0} - \frac{1}{{2,3k_{B} T}} \cdot \frac{\varepsilon - 1}{{2\varepsilon + 1}}\left( {\frac{{\mu_{1}^{2} }}{{r_{1}^{3} }} + \frac{{\mu_{2}^{2} }}{{r_{2}^{3} }} - \frac{{\mu_{ \ne }^{2} }}{{r_{ \ne }^{3} }}} \right)\), where ε is the permittivity of the medium; μ1, μ2, μ≠, r1, r2, r≠ are dipole moments and effective radii of reagents, products and transition states, respectively; kB is Boltzmann constant; T is absolute temperature [43].

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Acknowledgements

T. Pokidova is grateful to the Federal Research Center of Problems of Chemical Physics and Medical Chemistry of the Russian Academy of Sciences for financial support in calculating the parameters of the parabolic model (State assignment No. AAAA-A19-119071190045-0). M. Berezin is grateful to the Federal Research Center of Problems of Chemical Physics and Medical Chemistry of the Russian Academy of Sciences for financial support in measuring initiation rates in oxidizing unsaturated compounds by ESR method (State Assignment No. AAAA-A19-119041090087-4). E. Pliss, A. Sirik, A. Grobov, N. Pitsin, V. Machtin are grateful to the Russian Science Foundation for financial support in carrying out experiments to determine the rate constants of the oxidation of unsaturated compounds and calculations for kinetic and quantum chemical analysis of the detailed mechanism of the process (Grant No. 20-13-00148).

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Authors and Affiliations

  1. P.G. Demidov Yaroslavl State University, Yaroslavl, Russian Federation, 150003

    Eugene Pliss, Andrey Sirik, Alexey Grobov & Nikita Pitsyn

  2. Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Russian Federation, 142432

    Tamara Pokidova & Mikhail Berezin

  3. Yaroslavl State Technical University, Yaroslavl, Russian Federation, 150023

    Viacheslav Machtin & Mikhail Soloviev

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Pliss, E., Pokidova, T., Sirik, A. et al. Kinetic analysis of the reactivity of peroxyl radicals in chain oxidation of unsaturated compounds. Reac Kinet Mech Cat 137, 53–76 (2024). https://doi.org/10.1007/s11144-023-02524-7

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