| 裴玲,张海霞,张岩.没食子酸及其衍生物抗氧化活性的理论研究[J].井冈山大学自然版,2015,(4):27-33 |
| 没食子酸及其衍生物抗氧化活性的理论研究 |
| THEORY STUDY ON THE ANTIOXIDATION ACTIVITY OF GALLIC ACID AND ITS DERIVATIVES |
| 投稿时间：2015-04-04 修订日期：2015-06-01 |
| DOI：10.3969/j.issn.1674-8085.2015.04.006 |
| 中文关键词: 没食子酸 抗氧化性 解离能 密度泛函 |
| 英文关键词: gallic acid antioxidation dissociation enthalpy DFT |
| 基金项目:山东省滨州市科技发展计划项目(2014ZC0306),滨州学院科研基金项目(BZXYG1210) |
| 作者 | 单位 | E-mail | | 裴玲 | 滨州学院化学工程系, 山东, 滨州 256603
滨州市材料化学重点实验室, 山东, 滨州 256603 | peiling1201@163.com | | 张海霞 | 滨州学院化学工程系, 山东, 滨州 256603
滨州市材料化学重点实验室, 山东, 滨州 256603 | | | 张岩 | 滨州学院化学工程系, 山东, 滨州 256603
滨州市材料化学重点实验室, 山东, 滨州 256603 | |
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| 中文摘要: |
| 采用量子化学密度泛函理论(DFT)中的B3LYP方法在6-311+G(d,p)水平下对没食子酸(GA)及其衍生物没食子酸甲酯(MG)、没食子酸乙酯(EG)、没食子酸丙酯(PG)、没食子酸异丙酯(IPG)、没食子酸丁酯(BG)和没食子酸叔丁酯(TBG)进行了优化计算,从7个分子的几何结构、氢原子的NBO电荷、羟基解离能、电离势、HOMO、LUMO、ΔE(LUMO-HOMO)等方面分析了7种物质清除自由基的可能机理。结果表明,7种物质C(2)位的酚羟基为最大可能活性位点,容易发生抽氢反应,其次是C(1)位和C(3)位。抽氢反应表明,在非极性溶剂中其抗氧化能力大小为TBG > BG > IPG > PG > EG > MG > GA;电子转移机理表明,极性溶剂中其抗氧化能力大小为TBG > IPG > BG ≈ PG ≈ EG > MG > GA。 |
| 英文摘要: |
| The geometrical structures of gallic acid and its derivatives including methyl gallate (MG), ethyl gallate (EG), propyl gallate (PG), isopropyl gallate (IPG), butyl gallate (BG) and tertbutyl gallate (TBG) were calculated by using the Density Functional Theory (DFT) B3LYP method at the level of 6-311+G (d, p). The possible mechanism of scavenging free radicals of the seven compounds were discussed in detail based on the analysis of molecular structures, NBO charges on hydrogen atoms, the dissociation energy and ionization potential of O-H bonds, the energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), the energy gap between HOMO and LUMO, and etc. The calculated results showed that C2-OH should be the most active site for eliminating free radicals, next as the C1-OH and C3-OH. Pumping hydrogen reaction indicated that the order of the antioxidative activities of seven compounds in non-polar solvent listed as: TBG > BG > IPG > PG > EG > MG > GA. Electron transfer mechanism indicated that the order in polar solvent listed as: TBG > IPG > BG ≈ PG ≈ EG > MG > GA. |
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