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化学学报
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化学学报 ›› 2006, Vol. 64 ›› Issue (23): 2333-2338. 上一篇    下一篇

研究论文

分子旋光度的密度泛函计算及Soman绝对构型确定

丁晓琴*,1, 赵立峰2, 丁俊杰1, 陈冀胜1   

  1. (1北京药物化学研究所 北京 102205)
    (2上海交通大学化学化工学院 上海 200240)
  • 投稿日期:2005-10-09 修回日期:2005-12-29 发布日期:2006-12-14
  • 通讯作者: 丁晓琴

Calculation of Optical Rotation Using Density Functional Theory and Determination of Absolute Configuration for Soman

DING Xiao-Qin*,1; ZHAO Li-Feng2; DING Jun-Jie1; CHEN Ji-Sheng1   

  1. (1 Beijing Institute of Pharmaceutical Chemistry, Beijing 102205)
    (2 School of Chemistry & Chemical Technology, Shanghai Jiaotong University, Shanghai 200240)
  • Received:2005-10-09 Revised:2005-12-29 Published:2006-12-14
  • Contact: DING Xiao-Qin

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被引次数

5 | 1

手性化合物绝对构型的确定一直是有机化学特别是手性药物合成研究过程中经常遇到的问题之一. 利用密度泛函DFT/B3LYP量子化学计算方法, 通过计算两种已知旋光度分子的旋光度, 确认计算条件和验证计算结果的可靠性, 并将此方法应用于Soman旋光度的计算. 结合文献报道的Soman分子实验旋光度测定结果, 首次采用理论计算方法确定了梭曼(Soman)分子四个异构体的绝对构型, 分别为P(R),C(S)-Soman→P(＋)C(＋), P(R),C(R)-Soman→P(＋)C(－), P(S),C(S)-Soman→P(－)C(＋), P(S),C(R)-Soman→P(－)C(－).

关键词: 分子旋光度计算, DFT, 梭曼, 绝对构型

The determination of absolute configuration for chiral compounds is one of the most important problem in the organic chemisty, especially for chiral drug synthesis. Density functional theory (DFT/B3LYP) method with various basis sets were employed and verified by calculating the optical rotational properties of two tested chiral compounds, and than applied to the calculations of the optical rotational properties of soman to assign the absolute configuration of soman. The absolute configurations of four isomers for soman are P(R),C(S)-soman→P(＋)C(＋), P(R),C(R)-soman→P(＋)C(－), P(S),C(S)-soman→P(－)C(＋) and P(S),C(R)-soman→P(－)C(－).

Key words: calculation of optical rotation, density functional theory, soman, absolute configuration