title: Theoretical study of the peripheral disulfide bridge substituent effects on the antioxidant properties of naphthyridine diol derivatives.
abstract: The effect of a peripheral disulfide bridge substituent on the phenolic O-H bond dissociation energy (BDE) and the ionization potential (IP) of naphthyridine diol has been studied by density functional theory (DFT) calculation. Compared with naphthalene diol, the substituent of a peripheral disulfide bridge group is very efficient in reducing the BDE, whereas the insertion of nitrogen atoms into the naphthalenic ring only slightly changes the BDE of O-H bond but dramatically enhances the IP. It is similar with the stereoelectronic effect of the heterocyclic ring for the well-known alpha-tocopherol antioxidant and leads to a highly delocalized spin distribution. With the incorporation of these two aspects, a potential antioxidant is expected to be more active and more stable than alpha-tocopherol.
authors.affiliation: Central Laboratory, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China. esr@nankai.edu.cn
authors.forename: Ao
authors.initials: A
authors.lastname: Yu
authors.forename: Jian
authors.initials: J
authors.lastname: Wang
authors.forename: Xiaosong
authors.initials: X
authors.lastname: Xue
authors.forename: Yongjian
authors.initials: Y
authors.lastname: Wang
mesh_terms: D000465:Algorithms; D000975:Antioxidants / Q000737:chemistry*; D018011:Chalcogens / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry; D009287:Naphthyridines / Q000737:chemistry*; D011789:Quantum Theory; D013816:Thermodynamics
chemical_list: D000975:Antioxidants; D018011:Chalcogens; D004220:Disulfides; D005609:Free Radicals; D009281:Naphthalenes; D009284:Naphthols; D009287:Naphthyridines; C031721:naphthalene