Chiral Analysis by Tandem Mass Spectrometry Using the Kinetic Method, by Polarimetry, and by 1H NMR Spectroscopy

被引:7
作者
Fedick, Patrick W. [1 ]
Bain, Ryan M. [1 ]
Bain, Kinsey [1 ]
Cooks, R. Graham [1 ,2 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
[2] Purdue Univ, Ctr Analyt Instrumentat Dev, W Lafayette, IN 47907 USA
基金
美国国家科学基金会;
关键词
Second-Year Undergraduate; Analytical Chemistry; Laboratory Instruction; Organic Chemistry; Hands-On Learning/Manipulatives; Chirality/Optical Activity; Diastereomers; Enantiomers; Mass Spectrometry; NMR Spectroscopy; THERMOCHEMICAL DETERMINATIONS; STEREOCHEMISTRY; RESOLUTION; IBUPROFEN; DRUGS; ACIDS;
D O I
10.1021/acs.jchemed.7b00090
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The goal of this laboratory exercise was for students to understand the concept of chirality and how enantiomeric excess (ee) is experimentally determined using the analysis of ibuprofen as an example. Students determined the enantiomeric excess of the analyte by three different instrumental methods: mass spectrometry, nuclear magnetic resonance spectroscopy, and optical polarimetry. This laboratory exercise introduced mass spectrometry into the first-semester organic chemistry curriculum. Further, it allowed the students to compare and contrast the analytical figures of merit for each technique, a topic usually discussed later in chemistry courses. The ee resolution, sensitivity, limits of detection, and required sample preparation were considered. Furthermore, this laboratory experiment taught students how to use the kinetic method for chiral analysis by mass spectrometry, a new technique in a student laboratory exercise. Students' knowledge of how to select the appropriate technique for enantiomeric excess determination was broadened, as knowledge of the general concept of chirality, as seen in their laboratory reports and exit interviews.
引用
收藏
页码:1329 / 1333
页数:5
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