title: Density functional theory study of the structure-antioxidant activity of polyphenolic deoxybenzoins.
abstract: Quantum chemical calculations based on the density functional theory (DFT) have been employed to study the relationship between the structure and the antioxidant activity of four polyphenolic deoxybenzoins (DOBs) in solvents and the gas phase. The three main working mechanisms, H-atom transfer (HAT), single electron transfer-proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) have been investigated. The calculated results closely matched experimental values. The results obtained prove that for the HAT mechanism, the most efficient system possessed ortho-dihydroxy functionality. The results suggested that HAT would be the most favourable mechanism for explaining the radical-scavenging activity of polyphenolic DOBs in the gas phase, whereas the SPLET mechanism is the thermodynamically favourable pathway in polar solvents.
authors.affiliation: Chemical and Biological Pharmaceutical Engineering Research Center, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China; School of Pharmacy, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China. Electronic address: xueyunsheng@xzmc.edu.cn.
authors.forename: Yunsheng
authors.initials: Y
authors.lastname: Xue
authors.affiliation: Chemical and Biological Pharmaceutical Engineering Research Center, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China; School of Pharmacy, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China.
authors.forename: Youguang
authors.initials: Y
authors.lastname: Zheng
authors.affiliation: Chemical and Biological Pharmaceutical Engineering Research Center, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China; School of Pharmacy, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China.
authors.forename: Lin
authors.initials: L
authors.lastname: An
authors.affiliation: School of Pharmacy, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China.
authors.forename: Yunyan
authors.initials: Y
authors.lastname: Dou
authors.affiliation: Chemical and Biological Pharmaceutical Engineering Research Center, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China; School of Pharmacy, Xuzhou Medical College, No. 209, Tongshan Road, Xuzhou, Jiangsu 221004, China. Electronic address: njuliuyi2003@gmail.com.
authors.forename: Yi
authors.initials: Y
authors.lastname: Liu
mesh_terms: D000975:Antioxidants; D001573:Benzoin / Q000031:analogs & derivatives* / Q000737:chemistry; D010084:Oxidation-Reduction; D059808:Polyphenols; D011522:Protons; D012997:Solvents / Q000737:chemistry
chemical_list: D000975:Antioxidants; D059808:Polyphenols; D011522:Protons; D012997:Solvents; C492807:deoxybenzoin; D001573:Benzoin
keywords: Antioxidant mechanism; DFT; Deoxybenzoins; HAT; SET–PT; SPLET