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A New Method for Distinguishing between Enantiomers and Racemates and Assignment of Enantiomeric Purity by Means of Solid‐State NMR. Examples from Oxazaphosphorinanes
Author(s) -
Potrzebowski Marek J.,
Tadeusiak Elżbieta,
Misiura Konrad,
Ciesielski Włodzimierz,
Bujacz Grzegorz,
Tekely Piotr
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20021104)8:21<5007::aid-chem5007>3.0.co;2-b
Subject(s) - enantiomer , chemistry , isotropy , sideband , anisotropy , solid state nuclear magnetic resonance , nuclear magnetic resonance spectroscopy , tensor (intrinsic definition) , computational chemistry , stereochemistry , nuclear magnetic resonance , physics , optics , geometry , mathematics , quantum mechanics , microwave
It is shown that enantiomers and racemates that have identical isotropic NMR chemical shift as well as anisotropic chemical‐shift tensor parameters can be easily distinguished by means of the ODESSA ( O ne D imensional E xchange S pectroscopy by S ideband A lternation) technique. The method is based on the fact that the molecular symmetries and packing of enantiomers and racemates are usually significantly different. The power of the proposed approach is demonstrated by employing as model compounds P‐chiral oxazaphosphorine derivatives, which are widely used in clinical oncology. Correlation of the amplitude of the ODESSA decay (AOD) with enantiomeric excess is also presented.