高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

白藜芦醇清理羟基自由基夺氢机理的量子化学研究

申勇立1, 郝金库1,2, 曹映玉2, 杨鞔?SUP>2   

    1. 南开大学化学学院, 天津 300071;
    2. 天津师范大学化学与生命科学学院, 天津 300074
  • 收稿日期:2006-12-07 修回日期:1900-01-01 出版日期:2007-09-10 发布日期:2007-09-10
  • 通讯作者: 郝金库

Quantum Study on Abstracting Hydrogen Mechanism in Hydroxyl Radical Scavenging of Trans-resveratrol

SHEN Yong-Li1, HAO Jin-Ku1,2*, CAO Ying-Yu2, YANG En-Cui2   

    1. College of Chemistry, Nankai University, Tianjin 300071, China;
    2. College of Chemistry and Life Science, Tianjin Normal University, Tianjin 300074, China
  • Received:2006-12-07 Revised:1900-01-01 Online:2007-09-10 Published:2007-09-10
  • Contact: HAO Jin-Ku

PDF (PC)

被引次数

17

摘要： 在DFT方法的B3LYP/6-31G水平下, 对反式白藜芦醇分子的所有可能构象进行了优化, 并对最稳定构象进行了自然键轨道分析. 键级数据表明, 白藜芦醇清理羟基自由基最活泼反应位点应为其单羟基环上的羟基, 对产物白藜芦醇自由基的优化结果表明, 单羟基环氧自由基的稳定性最高. 在B3LYP/6-31G水平下寻找白藜芦醇单羟基环羟基清理羟基自由基的过渡态, 频率分析结果表明只存在一个虚频. 对该过渡态结构进行内禀反应坐标反应路径解析(IRC), 结果表明, 过渡态沿反应坐标方向分别指向反应物络合物和产物络合物, 反应通道各个能量驻点显示反应物与反应物络合物的能量差为E1=173.5193 kJ/mol, 反应物络合物与过渡态、反应物络合物与产物的能量差分别为Ea=16.5143 kJ/mol, E2=51.8799 kJ/mol. 可见反应物的能量远高于过渡态及产物, 因此, 反应物络合物的形成应是整个反应的驱动力.

关键词: 白藜芦醇, 抗氧化, 羟基自由基, 密度泛函理论, 内禀反应坐标反应路径解析

Abstract: All possible conformations of trans-resveratrol were optimized by using DFT B3LYP/6-31g, and natural bond analysis on the most stable conformation was carried out, the result shows that the most active position in the hydroxyl radical scavenging of trans-resveratrol was the phenolic hydroxyl in the single hydroxyl circle. The mechanism of this reaction has been theoretically studied at DFT B3LYP/6-31g. The IRC also has been carried out at the same theoretical level. The results show that the hydroxyl of trans-resveratrol reacted with hydroxyl radical to produce H2O. The energy of stationary points in the reaction path shows that the energy of reactant was E1=173.5193 kJ/mol, higher than that of the reactant complex, the activation energy was Ea=16.5143 kJ/mol, and the energy of product was E2=51.8799 kJ/mol, higher than that of the reactant complex. So when the reaction complex formed it would be trasformed into transition state and product immediately.

Key words: Resveratrol, Antioxidation, Hydroxyl radical, DFT, IRC

中图分类号: 

TrendMD: