Specific features of radical generation in the reaction of thiols with hydrogen peroxide

Zinatullina, K. M.; Касаикина, О. Т.; Motyakin, M. V.; Ionova, I. S.; Degtyarev, E. N.; Khrameeva, N. P.

doi:10.1007/s11172-020-2971-8

Cited by 9 publications

(5 citation statements)

References 42 publications

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“…We tend to think that MBT is easier to form free radicals than its anion M − and further coupled to generate MBTS. 20 At the same time, we also observed that when H 2 O 2 was added to the alkaline M-Na solution, the reaction solution turned yellow, implying that other products besides MBTS were formed.…”

Section: ■ Results and Discussionmentioning

confidence: 68%

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Main Reaction Network and Kinetics in the Synthesis of 2,2′-Dibenzothiazole Disulfide

Tian

Wang

et al. 2021

Ind. Eng. Chem. Res.

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The green synthesis of 2,2′-dibenzothiazole disulfide (MBTS) still faces some challenges. One of them is the fact that the main reaction network and kinetics have not been reported. In this paper, the characteristics of the mainly involved reactions were studied and the main reaction network for MBTS synthesis with hydrogen peroxide (H2O2) as an oxidant has been constructed. Some specific reaction conditions such as in high pH aqueous solution or in tert-butanol aqueous solution were designed to determine the reactions. The main reaction network includes a main reaction, a parallel side reaction, and the decomposition reactions of H2O2 and MBTS under alkaline conditions. The selectivity of the main reaction would be decreased with the increase of the pH value. The kinetic model was established, and the values of rate constants and activation energies were acquired. Furthermore, several general principles have been provided for the controllable preparation of MBTS.

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Section: ■ Results and Discussionmentioning

confidence: 68%

“…However, due to the poor solubility of MBT, the reaction cannot be controlled in a lower pH range (such as neutral or even weakly acidic). We tend to think that MBT is easier to form free radicals than its anion M – and further coupled to generate MBTS …”

Section: Resultsmentioning

confidence: 99%

Main Reaction Network and Kinetics in the Synthesis of 2,2′-Dibenzothiazole Disulfide

Tian

Wang

et al. 2021

Ind. Eng. Chem. Res.

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“…Both thiols contain carboxyl groups and form acidic solutions in water, thus, depending on the concentration of thiols, they can shift the pH of buff er solutions to the acidic values. 16 Previously, 32 it was found that with an increase in pH, the rate o f GSH consumption in the reaction with H 2 O 2 increases, the rate of radical formation decreases, and at pH 7, no radicals are formed.…”

Section: Resultsmentioning

confidence: 96%

“…Generation of thiyl radicals in the reactions of GSH and ASH with H 2 O 2 was found by ESR method us-Scheme 1 ing DMPO (5,5-dimethyl-1-pyr rolidine N-oxide) as a spin trap. 16 The rate of rad ical generation (W i ) in the ASH reaction with H 2 O 2 in deionized water were measured in a wide range of reagent concentrations by inhibitor method using a water-soluble acceptor (polymethine dye) with known spectral and kinetic properties. 15 Empirical functions of W i from thiol concentrations and H 2 O 2 for GSH (see lit.…”

Section: Resultsmentioning

confidence: 99%

“…The interaction of GSH with H 2 O 2 is a ccompanied by the formation of thiyl radicals. 16 The yield of radicals is low (~1%), but even in this amount they can initiate chain thiol-ene processes. The thio-ene reaction between GSH and unsatured phenols in the presence of hydrogen peroxide was studied 17 with resveratol (RVT), the properties and chemical behavior of which are of interest for medicine and pharmacy.…”

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confidence: 99%

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N-Acetylcysteine is an effective analog of glutathione in reactions with reactive oxygen species

et al. 2021

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The kinetic characteristics of the interaction of N-acetylcysteine (ASH) with reactive oxygen species (ROS), peroxyl radicals and hydrogen peroxide were determined. It was found that in terms of activity ASH in these reactions is similar to glutathione GSH, the main endogenous bioantioxidant. The kinetics of heat release in the interaction of GSH and ASH with H 2 O 2 was studied for the fi rst time by isothermal calorimetry. It is shown that the kinetic curves of heat release and changes in specifi c heat release rates practically coincide for both thiols taken in the stoichiometric ratio in the known reaction 2 TSH + H 2 O 2  TSST + 2 H 2 O.This indicates the relative autonomy of the S-H and S-S bonds in thiols and disulfi des, which are not aff ected by other groups in the molecule. At pH<7, ASH, like GSH, interacts with H 2 O 2 to form thiyl radicals, which initiate thiol-ene reactions with unsaturated phenol resveratrol. Under the same conditions, ASH ensures nearly the same radical initiation rates as GSH, and thiyl radicals from ASH are close in activity to GS • in chain propagation reactions.

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Effect of Lipophilic and Hydrophilic Thiols on the Lipid Oxidation

Касаикина

Zinatullina

Kancheva

et al. 2022

Lipid Oxidation in Food and Biological Systems

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Specific features of radical generation in the reaction of thiols with hydrogen peroxide

Cited by 9 publications

References 42 publications

Main Reaction Network and Kinetics in the Synthesis of 2,2′-Dibenzothiazole Disulfide

Main Reaction Network and Kinetics in the Synthesis of 2,2′-Dibenzothiazole Disulfide

N-Acetylcysteine is an effective analog of glutathione in reactions with reactive oxygen species

Effect of Lipophilic and Hydrophilic Thiols on the Lipid Oxidation

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