Central Laboratory, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
J Phys Chem A. 2010 Jan 21;114(2):1008-16. doi: 10.1021/jp908658z.
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.
通过密度泛函理论（DFT）计算研究了外围二硫键取代基对萘啶二醇酚 O-H 键离解能（BDE）和电离能（IP）的影响。与萘二醇相比，外围二硫键取代基在降低 BDE 方面非常有效，而将氮原子插入萘环中仅略微改变 O-H 键的 BDE，但会显著增强 IP。这与著名的α-生育酚抗氧化剂中环杂原子的立体电子效应相似，导致自旋分布高度离域。通过结合这两个方面，预期潜在的抗氧化剂将比α-生育酚更活跃、更稳定。
