核磁共振技术测定联萘酚的对映体纯度  

Determination of Enantiomeric Purity of Binaphthol by NMR Method

作　　者：奚忠华[1] 陆大东[1] 戴洁[1] 叶涛[1] 章文伟[1] Zhonghua Xi;Dadong Lu;Jie Dai;Tao Ye;Wenwei Zhang(National Demonstration Center for Experimental Chemistry Education(NanjingUniversity),Nanjing 210023,China.)

机构地区：[1]化学国家级实验教学示范中心(南京大学),南京210023

出　　处：《大学化学》2022年第2期180-185,共6页University Chemistry

基　　金：2021年基础学科拔尖学生培养计划2.0课题。

摘　　要：手性联萘酚((±)-BINOL)制备是国内高校常开设的一个实验,其产品的对映体纯度测试是实验的重要一环。以2-甲酰基苯硼酸和(S)-(−)-1-苯乙胺的混合物作为手性试剂与联萘酚发生Bull-James Assembly反应,以此设计了核磁共振氢谱(^(1)H NMR)测定联萘酚对映体纯度的实验。实验结果表明,通过反应生成的对映体混合物的核磁信号,能准确地计算出(±)-BINOL的对映体纯度。以选定的苯环氢核信号计算出的(R)-BINOL含量与理论ee值有着良好的线性关系(R^(2)=0.9999)。此实验方法能够快速完成大量学生样品的测量,同时大大减少实验废液的产生量。学生通过此实验可对核磁共振技术有更进一步的了解。The preparation of chiral binaphthol is a common experiment in colleges and universities,and the determination of enantiomeric purity is an important part of the experiment.The Bull-James Assembly between binaphthol and a mixture of 2-formylphenylboronic acid and(S)-(−)-1-phenylethylamine as chiral reagent was observed.Based on this,an experiment was designed to determine the enantiomer purity of binaphthol via ^(1)H NMR.The results show that the enantiomer purity of(±)-BINOL can be accurately calculated from the NMR signals of the enantiomer mixture generated by the reaction.There is a good linear relationship(R^(2)=0.9999)between the(R)-BINOL ratio calculated from the selected proton signal and the given ee value.This method can quickly complete the measurement of a large number of student samples,and produce a small amount of waste liquid.Students can have a further understanding of NMR technology through this experiment.

关 键 词：核磁共振 联萘酚 对映体纯度 对映体过量 

分 类 号：G64[文化科学—高等教育学] O6[文化科学—教育学]