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Resolution of trans-Cyclohexane-1,2-diamine and Determination of the Enantiopurity Using Chiral Solid-Phase HPLC Techniques and Polarimetry
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Abstract
This experiment entails the resolution of trans-cyclohexane-1,2-diamine using either enantiomer of tartaric acid and the determination of the optical purity by HPLC and polarimetry. The experiment is designed to reinforce and broaden the students' understanding of the relationship between enantiomers and diasteriomers and of diasteriomeric interactions. Additionally, it illustrates the differences in physical properties (solubility and melting range) between a racemic mixture and the same compound in highly resolved form. The techniques employed herein for the determination of optical purity continue to be widely used in asymmetric synthesis and prove essential for the determination of the enantiomeric excess of a non-racemic mixture. The experiment also includes the synthesis of the bisamide of trans-cyclohexane-1,2-diamine.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Analytical ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
ChromatographyCiting Articles
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This article has been cited by 10 ACS Journal articles (5 most recent appear below).
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- Received: August 03, 2009
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