Please use this identifier to cite or link to this item: https://doi.org/10.1021/jp057315r
Title: Investigation of the influence of hydroxy groups on the radical scavenging ability of polyphenols
Authors: Thavasi, V. 
Leong, L.P. 
Bettens, R.P.A. 
Issue Date: 13-Apr-2006
Source: Thavasi, V., Leong, L.P., Bettens, R.P.A. (2006-04-13). Investigation of the influence of hydroxy groups on the radical scavenging ability of polyphenols. Journal of Physical Chemistry A 110 (14) : 4918-4923. ScholarBank@NUS Repository. https://doi.org/10.1021/jp057315r
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. © 2006 American Chemical Society.
Source Title: Journal of Physical Chemistry A
URI: http://scholarbank.nus.edu.sg/handle/10635/112608
ISSN: 10895639
DOI: 10.1021/jp057315r
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