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<p>A computational analysis using DFT/B3LYP was performed to evaluate the antioxidant capacities and mechanisms of 16 flavonoid derivatives, employing the 6-311 + + G** basis set. Three antioxidant mechanisms were investigated: sequential proton loss electron transfer (SPLET), single-electron transfer–proton transfer (SET-PT), and hydrogen atom transfer (HAT). These mechanisms were examined in the gas phase, as well as in water, DMSO, and ethanol. Energy descriptors, including bond dissociation enthalpy (BDE), ionization potential (IP), electron transfer energy (ETE), proton dissociation enthalpy (PDE), and proton affinity (PA), were calculated. The HAT mechanism was found to be the most thermodynamically favorable in the gas phase, exhibiting the lowest BDE value of 71.31&#xa0;kcal/mol. In water, the SPLET mechanism was predominant, presenting the lowest PA + ETE value of 108.32&#xa0;kcal/mol. In DMSO, the SET-PT pathway was the most favorable, with a minimum IP + PDE value of 107.40&#xa0;kcal/mol. Additionally, the presence and positioning of hydroxyl groups—particularly at the 4′ and 7 positions—greatly influenced the antioxidant potential of the studied compounds.</p>

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Thermodynamics Aspects of Free Radical Scavenging Mechanisms of Flavonoids Derivatives, a Computational Study

  • 期刊论文

  • 发表日期：

    2025年8月8日

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  • Houria Djeradi,
  • Ali Rahmouni,
  • Abdelkrim Cheriti

摘要

A computational analysis using DFT/B3LYP was performed to evaluate the antioxidant capacities and mechanisms of 16 flavonoid derivatives, employing the 6-311 + + G** basis set. Three antioxidant mechanisms were investigated: sequential proton loss electron transfer (SPLET), single-electron transfer–proton transfer (SET-PT), and hydrogen atom transfer (HAT). These mechanisms were examined in the gas phase, as well as in water, DMSO, and ethanol. Energy descriptors, including bond dissociation enthalpy (BDE), ionization potential (IP), electron transfer energy (ETE), proton dissociation enthalpy (PDE), and proton affinity (PA), were calculated. The HAT mechanism was found to be the most thermodynamically favorable in the gas phase, exhibiting the lowest BDE value of 71.31 kcal/mol. In water, the SPLET mechanism was predominant, presenting the lowest PA + ETE value of 108.32 kcal/mol. In DMSO, the SET-PT pathway was the most favorable, with a minimum IP + PDE value of 107.40 kcal/mol. Additionally, the presence and positioning of hydroxyl groups—particularly at the 4′ and 7 positions—greatly influenced the antioxidant potential of the studied compounds.