A DFT Computational Study of the Antioxidant Activities Exhibited by 3-aryl-4-hydroxycoumarin Derivatives
Journal Title: Journal of Chemistry and Applied Biochemistry - Year 2016, Vol 3, Issue 1
Abstract
Density functional theory (DFT) was employed to obtain energy (E), ionization potential (IP), bond dissociation enthalpy (BDE) of O-H bond and stabilization energy (∆Eiso) in order to infer the scavenging activity of 3-phenyl-4-hydroxy coumarin derivatives. Spin density calculations were also performed for the proposed antioxidant activity mechanism. The unpaired electron formed by the hydrogen abstraction from the phenolic hydroxyl group of 3-phenyl-4-hydroxy coumarin derivatives localized on the phenolic oxygen at positions 4 and 3’, the C3 carbon, the C2’ and C6’ carbon atoms at ortho positions and C4’ carbon atom at para position. The lowest phenolic oxygen contribution corresponded to the highest scavenging activity value. It was found that antioxidant activity depends on the presence of a phenyl group at position 3 of coumarin skeleton and presence of a hydroxyl at the C4 and C3’. In addition, the presence of chlorine atom at position 6 on the coumarin skeleton leads to decrease O-H BDE and increase antioxidant activity significantly. There is a correlation between IP and O-H BDE and the capacity of scavenging peroxy radicals and the percentage of the hydroxyl radical scavenging activity.
Authors and Affiliations
Mansour H Almatarneh
Keywords
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A DFT Computational Study of the Antioxidant Activities Exhibited by 3-aryl-4-hydroxycoumarin Derivatives
Density functional theory (DFT) was employed to obtain energy (E), ionization potential (IP), bond dissociation enthalpy (BDE) of O-H bond and stabilization energy (∆Eiso) in order to infer the scavenging activity of 3-p...