Chemical Sciences: A Manual for CSIR-UGC National Eligibility Test for Lectureship and JRF/NMR spectroscopy of stereoisomers
This page was imported and needs to be de-wikified. Books should use wikilinks rather sparsely, and only to reference technical or esoteric terms that are critical to understanding the content. Most if not all wikilinks should simply be removed. Please remove {{dewikify}} after the page is dewikified. |
NMR spectroscopy techniques can determine the absolute configuration of stereoisomers such as cis or trans alkenes, R or S enantiomers, and R,R or R,S diastereomers.[1][2]
In a mixture of enantiomers, these methods can help quantify the optical purity by integrating the area under the NMR peak corresponding to each stereoisomer. Accuracy of integration can be improved by inserting a chiral derivatizing agent with a nucleus other than hydrogen or carbon, then reading the heteronuclear NMR spectrum: for example fluorine-19 NMR or phosphorus-31 NMR. Mosher's acid contains a -CF3 group, so if the adduct has no other fluorine atoms, the 19F NMR of a racemic mixture shows just two peaks, one for each stereoisomer.
As with NMR spectroscopy in general, good resolution requires a high signal-to-noise ratio, clear separation between peaks for each stereoisomer, and narrow line width for each peak. Chiral lanthanide shift reagents cause a clear separation of chemical shift, but they must be used in low concentrations to avoid line broadening.
Methods[edit | edit source]
- Karplus equation
- Chiral derivatizing agent
- Mosher's acid
- Chiral solvating agent
- Chiral lanthanide shift reagent (e.g. Eufod)
- NMR database method
References[edit | edit source]
- ↑ David Parker. "NMR determination of enantiomeric purity." Chem. Rev. 1991, 91, 1441–1457. [1]
- ↑ Frank J. Hollis. "NMR Through the Looking Glass: Uses of NMR Spectroscopy in the Analysis and Synthesis of Chiral Pharmaceuticals." 1994. [2]