Antioxidant activity of 4-[alkyl(benzyl)sulfanylmethyl]-5-methyl-2,4-dihydro-3H-pyrazol-3-ones

• Published in: Russian chemical bulletin 2023-10, Vol.72 (10), p.2508-2512
• Main Authors: Yakupova, L. R., Migranov, A. R., Baeva, L. A., Safiullin, R. L.
• Format: Article
• Language: English
• Subjects: Antioxidants; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Coefficients; Full Articles; Hydroxyl groups; Inhibitors; Inorganic Chemistry; Organic Chemistry; Oxidation; Pyrazole; Pyrazolones; Stoichiometry; Sulfur
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-023-4053-1

In order to search for efficient antioxidants of the pyrazolone series, sulfur-containing derivatives of 2,4-dihydro-3 H -pyrazol-3-one and 1 H -pyrazole ( 1a–e ) were studied in the model system of radical chain oxidation of 1,4-dioxane. The antioxidant activity of these compounds was determined. The rate constant for the reaction of peroxyl radicals with inhibitor 1 ( k 7 ) and stoichiometric inhibition coefficient ( f ) were calculated at 333 K. Sulfur-containing 2,4-dihydro-3 H -pyrazol-3-ones exhibit a higher antioxidant activity fk 7 = (5.7–9.2)·10 4 L mol −1 s −1 ) than 4-(pentylsulfanylmethyl)-3,5-dimethyl-1 H -pyrazole fk 7 ⩽ 2 · 10 3 L mol −1 s −1 ), which is possibly due to the presence of the hydroxyl group in the pyrazolone cycle in the hydroxy form. The stoichiometric coefficients of inhibition for 4-(benzylsulfanylmethyl)-5-methyl-, 5-methyl-4-(pentylsulfanylmethyl)-, and 5-methyl-4-(propylsulfanylmethyl)-2,4-dihydro-3 H -pyrazol-3-ones f = 0.95–1.3) indicate the “decay” of one peroxyl radical on one inhibitor molecule. In the case of 5-methyl-4-[(2-propylsulfanyl)methyl]-2,4-dihydro-3 H -pyrazol-3-one, the stoichiometric coefficient of inhibition decreases f = 0.59).