Isolable atropisomers of 2-aryl indoline derivatives: determination of rotational barrier by density functional theory approach
Tetrahedron(2014)
摘要
The rotational process of 2-aryl ring in 1-acyl-2-aryl-3,3-dimethylindolines was determined by density functional theory (DFT) at B3LYP/6-31G(d) level. The calculated barrier height for the rotational process of [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethylindolin-1-yl]phenylmethanone (1) was ca. 30 kcal/mol, comparable to the previously reported experimental values of 26–28 kcal/mol for the corresponding derivatives. The Hartree–Fock (HF) calculation overestimated the barrier. The DFT-calculated rotational barrier height provided valuable information for knowing whether the conformers were isolable or not. The transition structure analyses showed that the presence of 2,6-substituents on the aryl ring is essential for the isolation of the conformers at room temperature. Based on the DFT-calculated geometries, the rotational process and the intramolecular weak interactions in the restricted rotation were analyzed.
更多查看译文
关键词
1-Acyl-2-aryl-3,3-dimethylindoline,Diastereomeric atropisomer,Restricted rotation,Density functional theory calculation
AI 理解论文
溯源树
样例
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
生成溯源树,研究论文发展脉络
Chat Paper
正在生成论文摘要