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• W2063809137 endingPage "4923" @default.
• W2063809137 startingPage "4918" @default.
• W2063809137 abstract "Recently, O−H bond dissociation enthalpies (BDEs) have been successfully used to express the free radical scavenging ability of polyphenolic antioxidants. In this work, the BDEs of phenol, catechol, resorcinol, hydroquinone, pyrogallol, phloroglucinol, 1,2,4-benzenetriol, and 5-hydroxypyrogallol have been calculated at B3LYP/6-311G++(3df, 3pd) and used to elucidate the effect of OH groups. Increasing the number of OH groups in the adjacent (vicinal) position decreases the BDE of phenols. Increasing the number of O−H groups in the alternative position C(1,3) as in resorcinol and C(1,3,5) as in phloroglucinol does not show any notable change in the BDEs when compared to that of OH in C(1) as in phenol. 5-Hydroxypyrogallol has the smallest BDE (250.3 kJ mol-1) followed by pyrogallol (289.4 kJ mol-1), then 1,2,4-benzenetriol (294.8 kJ mol-1), and then catechol (312.8 kJ mol-1). Overall, our results indicated that the presence of ortho and para hydroxy groups reduces the BDEs. An intramolecular hydrogen bond (IHB) develops due to the ortho arrangement of OH's and plays a dominant role in decreasing the BDEs. This key study on phenols showed that the reactive order of OH position in the benzene ring is the following: 5-hydroxypyrogallol > pyrogallol > 1,2,4-benzenetriol > catechol > hydroquinone ≫ phenol ∼ resorcinol ∼ phloroglucinol." @default.
• W2063809137 created "2016-06-24" @default.
• W2063809137 creator A5045145914 @default.
• W2063809137 creator A5047363342 @default.
• W2063809137 creator A5082795449 @default.
• W2063809137 date "2006-03-17" @default.
• W2063809137 modified "2023-09-27" @default.
• W2063809137 title "Investigation of the Influence of Hydroxy Groups on the Radical Scavenging Ability of Polyphenols" @default.
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• W2063809137 doi "https://doi.org/10.1021/jp057315r" @default.
• W2063809137 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16599462" @default.
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