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Effect of Solvent Polarity on the Synergistic Effects in Radical Oxidation of Natural Phenols in the Presence of Mono- and Oligosaccharides

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

As shown by photocolorimetry, NMR spectroscopy, and calculations based on the density functional theory, the synergistic antiradical effect of binary formulations of vegetable phenols with mono- and oligosaccharides in deactivation of 2,2ʹ-diphenyl-1-picrylhydrazyl in aprotic solvents consists in the formation of a phenol–saccharide hydrogen-bonded complex with more pronounced reducing properties compared to the components taken separately. In benzene, the synergistic effect for all the phenol–saccharide combinations studied is weak (no more than 30%) or is not observed at all. With an increase in the polarity of the aprotic solvent, the maximal synergistic effect increases, and for 80 : 20 (v/v) 3-pyrogallolcarboxylic acid–maltotriose and ferulic acid–maltotriose mixtures in dimethyl sulfoxide it reaches 65–68%. One-factor linear dependences of the synergistic effect on the ionization potential of the phenol component of the mixture were determined. The correlation obtained can serve as a basis for evaluating the radical performance of natural phenol–carbohydrate synergistic formulations.

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ACKNOWLEDGMENTS

The DFT calculations were performed at the Center for Shared Use High-Performance Calculations, Southern Federal University. The authors are grateful to Prof. I.N. Shcherbakov, Head of the Kogan Chair of Physical and Colloidal Chemistry, Southern Federal University, for the assistance in quantum-chemical calculations.

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Authors and Affiliations

  1. Donetsk National University, 283001, Donetsk, Russia

    N. I. Belaya, A. V. Belyi & E. A. Budnikova

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  1. N. I. Belaya
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  2. A. V. Belyi
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  3. E. A. Budnikova
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Correspondence to N. I. Belaya.

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Translated from Zhurnal Prikladnoi Khimii, No. 10, pp. 1320–1328, October, 2022 https://doi.org/10.31857/S0044461822100115

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Belaya, N.I., Belyi, A.V. & Budnikova, E.A. Effect of Solvent Polarity on the Synergistic Effects in Radical Oxidation of Natural Phenols in the Presence of Mono- and Oligosaccharides. Russ J Appl Chem 95, 1611–1617 (2022). https://doi.org/10.1134/S1070427222100123

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