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Investigation of the radical scavenging potency of hydroxybenzoic acids and their carboxylate anions

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Abstract

In this article, the antoxidative mechanisms HAT, SPLET, and SET-PT of the ortho-, meta-, and para-hydroxybenzoic acids and corresponding carboxylate anions with different radicals (·OO−, ·OH, ·OOH, and CH3OO·) were investigated. For this reason, the ΔH BDE, ΔH IP, and ΔH PA values of the corresponding reactions in different solvents (water, DMSO, pentylethanoate, and benzene) were examined. For this purpose, the M05-2X/6-311++G(d,p) and B3LYP-D2/6-311++G(d,p) theoretical models were applied. Although the B3LYP-D2 method produced lower reaction enthalpy values, both theoretical models exhibited the same trend. It was found that SET-PT is not a favorable reaction path for any hydroxybenzoic acids and their anions with any radicals in any solvents. No anion reacts with −·O2, whereas meta- and para-hydroxybenzoic acids react with −·O2 only in nonpolar solvents. In all other cases, the HAT and SPLET mechanisms are competitive. Which of them is dominant depends on the properties of the acids, anions, radicals, and solvents.

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Acknowledgments

The authors gratefully acknowledge financial support from the Ministry of Science of the Republic of Serbia (project Nos. 172015 and 174028) and the Ministry of Science, Education, and Sports of the Republic of Croatia (project Nos. 079-0000000-3211 and 098-0982464-2511).

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Authors and Affiliations

  1. Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadžića bb, 36300, Novi Pazar, Republic of Serbia

    Zoran Marković

  2. Bioengineering Research and Development Center, 34000, Kragujevac, Republic of Serbia

    Jelena Đorović

  3. Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000, Belgrade, Republic of Serbia

    Jasmina M. Dimitrić Marković

  4. Faculty of Biology, University of Belgrade, Studentski trg 12-16, 11000, Belgrade, Republic of Serbia

    Miroslav Živić

  5. Faculty of Agriculture, The Josip Juraj Strossmayer University, P.O. Box 719, 31107, Osijek, Croatia

    Dragan Amić

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  1. Zoran Marković
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  2. Jelena Đorović
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  3. Jasmina M. Dimitrić Marković
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  4. Miroslav Živić
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  5. Dragan Amić
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Correspondence to Zoran Marković.

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Marković, Z., Đorović, J., Dimitrić Marković, J.M. et al. Investigation of the radical scavenging potency of hydroxybenzoic acids and their carboxylate anions. Monatsh Chem 145, 953–962 (2014). https://doi.org/10.1007/s00706-014-1163-3

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  • DOI: https://doi.org/10.1007/s00706-014-1163-3

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