Trans-resveratrol establishes the planarity in its structure which makes it an interesting compound in both experimental and theoretical examinations. The current study, using the density functional method (DFT), attempts to compare the antioxidative capacities between hydroxyl (OH) and aromatic methine (CH) groups of this molecule. Becke’s exchange-correlation B3LYP functional together with 6-311++G(d, p) basis set was used to reveal the effects of structural geometry and electronic feature on the antioxidative results of OH and CH groups. The antioxidative action of trans-resveratrol has followed the HAT mechanism in gas, but the SPLET pathway in liquids. OH bond breaking is easier than CH bond disruption. 4-OH bond breaking induces the lowest BDE values of 74.4–77.9 kcal/mol in gas, acetone, methanol, and water, as well as the lowest PA values of 37.2–46.2 kcal/mol in acetone, methanol, and water. From the kinetic view, 4-OH is also an active center to capture laboratory radical DPPH, ROS radicals HOO• and CH3O•, and RNS radical •NO2.

中文翻译：

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反式白藜芦醇的抗氧化剂：基于热力学观点的 OH 和 CH 基团比较

反式白藜芦醇在其结构中建立了平面性，这使得它在实验和理论检验中都是一个有趣的化合物。目前的研究使用密度泛函方法 (DFT)，试图比较该分子的羟基 (OH) 和芳香次甲基 (CH) 基团之间的抗氧化能力。Becke 的交换相关 B3LYP 泛函与 6-311++G(d, p) 基组一起用于揭示结构几何和电子特征对 OH 和 CH 基团抗氧化结果的影响。反式白藜芦醇的抗氧化作用在气体中遵循 HAT 机制，而在液体中遵循 SPLET 途径。OH 键断裂比 CH 键断裂更容易。4-OH 键断裂导致气体、丙酮、甲醇和水中的 BDE 值最低，为 74.4–77.9 kcal/mol，以及在丙酮、甲醇和水中的最低 PA 值 37.2–46.2 kcal/mol。从动力学角度看，4-OH也是捕获实验室自由基DPPH、ROS自由基HOO•和CH3O•和RNS自由基•NO2的活性中心。