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Chiral recognition of nitriles by 1 H NMR spectroscopy in the presence of a chiral dirhodium complex
Author(s) -
Hameed Shahid,
Ahmad Roshan,
Duddeck Helmut
Publication year - 1998
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199806)36:13<s47::aid-omr290>3.0.co;2-j
Subject(s) - chemistry , diastereomer , trifluoromethyl , enantiomer , rhodium , nuclear magnetic resonance spectroscopy , stereochemistry , proton nmr , nitrile , chirality (physics) , medicinal chemistry , organic chemistry , catalysis , nambu–jona lasinio model , physics , quark , alkyl , quantum mechanics , chiral symmetry breaking
The 1 H NMR spectra of a variety of chiral racemic nitriles were recorded in CDCl 3 in the absence and presence of dirhodium tetra‐( R )‐α‐methoxy‐α‐(trifluoromethyl)phenylacetate [Rh 2 (MTPA) 4 ; MTPA≡Mosher’s acid]. Moderate 1 H signal shifts but clear diastereomeric dispersions due to complexation were observed which allow the determination of the enantiomeric ratio of the nitriles. Tentative statements concerning the complexing mode of the cyano group at the rhodium atom (side‐on vs . end‐on) are presented. © 1998 John Wiley & Sons, Ltd.