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A Simple 13 C NMR Method for the Discrimination of Complex Mixtures of Stereoisomers: All Eight Stereoisomers of α‐Tocopherol Resolved
Author(s) -
Lankhorst Peter P.,
Netscher Thomas,
Duchateau Alexander L. L.
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22535
Subject(s) - chemistry , chloroform , tocopherol , nuclear magnetic resonance spectroscopy , proton nmr , simple (philosophy) , stereochemistry , computational chemistry , organic chemistry , analytical chemistry (journal) , vitamin e , antioxidant , philosophy , epistemology
A simple one‐dimensional 13 C NMR method is presented to discriminate between stereoisomers of organic compounds with more than one chiral center. By means of this method it is possible to discriminate between all eight stereoisomers of α‐tocopherol. To achieve this the chiral solvating agent ( S )‐(+)‐1‐(9‐anthryl)‐2,2,2‐trifluoroethanol and the compound of interest were dissolved in high concentrations in chloroform‐d, and the nuclear magnetic resonance (NMR) spectrum was recorded at a low temperature. The individual stereoisomers of α‐tocopherol were assigned by spikes of the reference compounds. The method was also applied to six other representative examples. Chirality 27:850–855, 2015 . © 2015 Wiley Periodicals, Inc.