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Reactivity of Peroxyl Radicals with 5-Methyl-4-[(Propylsulfanyl)methyl]-2,4-Dihydro-3H-Pyrazol-3-one

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Abstract

5-Methyl-4-[(propylsulfanyl)methyl]-2,4-dihydro-3H-pyrazol-3-one was shown to inhibit the radical-chain peroxidation of 1,4-dioxane, ethylbenzene, and methyl oleate. One peroxyl radical is trapped by each (propylsulfanylmethyl)-substituted 2,4-dihydro-3H-pyrazol-3-one molecule. The reaction rate constant of the compound with a peroxyl radical depends on the structure of the latter and decreases in the series: peroxyl radical of 1,4-dioxane, ethylbenzene, and methyl oleate (k7 × 104, L mol –1 s–1, 333 K: 5.7, 4.1, 1.1). The reason for the observed dependence was discussed.

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Funding

This study was performed under the research plan at Ufa Institute of Chemistry, Ufa Research Center, Russian Academy of Sciences (topic “Kinetics and mechanisms of reactions involving nitroso oxides and peroxyl radicals” АААА-А17-117011910034-8).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Bashkortostan, Russia

    L. R. Yakypova, L. A. Baeva & R. L. Safiullin

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  1. L. R. Yakypova
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  2. L. A. Baeva
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  3. R. L. Safiullin
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Correspondence to L. R. Yakypova.

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Translated by L. Smolina

Abbreviations and notation: AIBN, 2,2'-azo-bis(isobutyronitrile); 3Н-pyrazol-3-one, 5-methyl-4-[(propylsulfanyl)methyl]-2,4-dihydro-3Н-pyrazol-3-one; DMSO-d6, dimethyl sulfoxide-d6; TMS, tetramethylsilane; τ, induction period; F, degree of the inhibiting action of inhibitor; wi, initiation rate; w0, noninhibited oxidation rate; w, inhibited oxidation rate; f, stoichiometric coefficient of inhibition; ki, initiation rate constant; k1 and k2, chain propagation rate constants; kd, initiator decay rate constant; k6, rate constant of oxidation chain termination by recombination of peroxyl radicals; k7, inhibition rate constant; [InH], initial concentration of 3Н‑pyrazol-3-one, RH, oxidized substrate (1,4-dioxane, ethylbenzene, methyl oleate); R•, \({\text{RO}}_{{\text{2}}}^{\bullet }{\text{,}}\) ROOH, alkyl and peroxyl radicals and hydroperoxide formed from the substrate.

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Yakypova, L.R., Baeva, L.A. & Safiullin, R.L. Reactivity of Peroxyl Radicals with 5-Methyl-4-[(Propylsulfanyl)methyl]-2,4-Dihydro-3H-Pyrazol-3-one. Kinet Catal 62, 56–61 (2021). https://doi.org/10.1134/S0023158421010134

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