高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (8): 1559.doi: 10.7503/cjcu20150151

• 物理化学 • 上一篇    下一篇

振动圆二色谱在轴手性β-双咔啉N—O衍生物立体化学研究中的应用

朱华结1(), 刘莉2, 杨芹1   

  1. 1. 河北大学药学院, 2. 生命科学学院, 保定 071002
  • 收稿日期:2015-02-12 出版日期:2015-08-10 发布日期:2015-07-17
  • 作者简介:联系人简介: 朱华结, 男, 博士, 教授, 主要从事天然有机化学、 不对称合成化学及理论计算研究. E-mail:hjzhu@mail.kib.ac.cn

Vibrational Circular Dichroism in Study of Stereochemistry of Chiral β-Biscarboline with N—O Functional Group

ZHU Huajie1,*(), LIU Li2, YANG Qin1   

  1. 1. College of Pharmacy, 2. School of Life Science, Hebei University, Baoding 071002, China
  • Received:2015-02-12 Online:2015-08-10 Published:2015-07-17
  • Contact: ZHU Huajie E-mail:hjzhu@mail.kib.ac.cn

摘要:

采用振动圆二色谱(VCD)方法研究了一个具有高度催化活性的轴手性结构的双咔啉N—O化合物的立体化学结构. 在B3LYP/6-311+G(d)水平上得到的计算结果表明, 对于具有负旋光值的双咔啉N—O化合物化合物, 其绝对构型是aS. 同时, 分别计算了双咔啉N—O化合物的电子圆二色谱(ECD)和旋光值, 并与实验结果进行了比较. 在化合物结构完全正确条件下, VCD, ECD和旋光数据均表明, 具有负旋光值的该化合物的绝对构型是aS.

关键词: 振动圆二色谱, 轴手性, β-双咔啉, 绝对构型

Abstract:

Vibrational circular dichroism(VCD) was applied for study of the absolute configuration of chiral axial bis-carboline with N—O function. The computational results exhibite that (-)-biscarboline derivative should have aS absolute configuration. At the same time, electronic circular dichroism(ECD) and optical rotation(OR) methods were also used to study its absolute configuration. The results show that the three diffe-rent conclusion from VCD, ECD and OR methods should give a same conclusion, namely, this (-)-biscarboline derivative should have aS absolute configuration.

Key words: Vibrational circular dichroism(VCD), Axial chirality, β-Biscarboline, Absolute configuration

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