sp~2碳自由基环合成构建N杂环化合物的机理研究
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摘要
本论文采用密度泛函方法对SP~2杂化的碳芳基自由基的分子内环合成反应机理进行了理论研究，研究体系包含N-甲基-N-(N-甲基吲哚酰)-2-苯胺自由基、N-甲基-N-呋喃酰-2-苯胺自由基和N-甲基-N-(N-甲基-N-苯基甲酰)-2-苯胺自由基。理论研究得到了相应的反应势能面，主要从动力学和热力学效应的贡献、环化过程中结构参数的改变以及电子轨道作用等角度解释了芳基自由基分子内环合成反应的区域选择性和反应机理。研究结果表明，目前的理论研究方法可以正确预测自由基环合成反应过程的机理、中间体结构、产物分布、本征势垒、热力学对动力学的贡献、电子进攻反应中轨道的变化等关键物理量。利用这种方法和技术，可以正确预测所设计的自由基反应的选择性和趋势，为合成目标的选择提供直接的有效信息。
In this thesis, intramolecular radical cyclization mechanism of SP~2-carbon arylswere investigated by using of DFT methods. N-methyl-N-(N-methylindoacyl)aniline-2-yl radical, N-methyl-N-furanacyl-aniline-2-yl radical, and N-methyl-N-(N-methyl-N-phenylcarbamoyl)aniline-2-yl radical were selected as target systems. Theoreticalinverstigation results provided corresponding reaction potential energy surfaces andreaction pathways of aryl radical intramolecular cyclizations. Furthermore, theregioselectivity and reaction mechanism were also explained by the contribution ofkinetic and thermodynamic effects, changes of structural parameters of key species inradical cyclizations, and corresponding orbital interaction energies. The results showedthat the present theoretical methods can correctly predict the mechanism ofintramolecular radical cyclizations, intermediate geometries, product distributions, intrinsic barriers, the thermodynamics contribution to the dynamics, and the changes inorbitals of electronic attack reactions. By the methods and technologies, one cancorrectly predict the reaction selectivity and trend of intramolecular radical cyclizations,and the given theoretical information can directly provide availably experimental targetsfor organic systhesis chemists.
In this thesis, intramolecular radical cyclization mechanism of SP~2-carbon arylswere investigated by using of DFT methods. N-methyl-N-(N-methylindoacyl)aniline-2-yl radical, N-methyl-N-furanacyl-aniline-2-yl radical, and N-methyl-N-(N-methyl-N-phenylcarbamoyl)aniline-2-yl radical were selected as target systems. Theoreticalinverstigation results provided corresponding reaction potential energy surfaces andreaction pathways of aryl radical intramolecular cyclizations. Furthermore, theregioselectivity and reaction mechanism were also explained by the contribution ofkinetic and thermodynamic effects, changes of structural parameters of key species inradical cyclizations, and corresponding orbital interaction energies. The results showedthat the present theoretical methods can correctly predict the mechanism ofintramolecular radical cyclizations, intermediate geometries, product distributions, intrinsic barriers, the thermodynamics contribution to the dynamics, and the changes inorbitals of electronic attack reactions. By the methods and technologies, one cancorrectly predict the reaction selectivity and trend of intramolecular radical cyclizations,and the given theoretical information can directly provide availably experimental targetsfor organic systhesis chemists.
引文
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