期刊
JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN
卷 27, 期 11, 页码 951-964出版社
SPRINGER
DOI: 10.1007/s10822-013-9692-0
关键词
Schiff bases; Antioxidant; DFT; Kinetics; Free radical scavenging; BDE; Structure-activity relationship
资金
- Ministry of Education, Youth and Sports of the Czech Republic [CZ.1.05/2.1.00/03.0058]
- 'Association Djerbienne de France' (ADF)
Phenolic Schiff bases are known for their diverse biological activities and ability to scavenge free radicals. To elucidate (1) the structure-antioxidant activity relationship of a series of thirty synthetic derivatives of 2-methoxybezohydrazide phenolic Schiff bases and (2) to determine the major mechanism involved in free radical scavenging, we used density functional theory calculations (B3P86/6-31+(d,p)) within polarizable continuum model. The results showed the importance of the bond dissociation enthalpies (BDEs) related to the first and second (BDEd) hydrogen atom transfer (intrinsic parameters) for rationalizing the antioxidant activity. In addition to the number of OH groups, the presence of a bromine substituent plays an interesting role in modulating the antioxidant activity. Theoretical thermodynamic and kinetic studies demonstrated that the free radical scavenging by these Schiff bases mainly proceeds through proton-coupled electron transfer rather than sequential proton loss electron transfer, the latter mechanism being only feasible at relatively high pH.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据