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Determination of enantiomeric composition of (−)‐( R )‐2‐ tert ‐butyltetrahydroimidazolidin‐4‐one by polarimetry, 1 H NMR, and chiral SFC
Author(s) -
GarciaMartinez Cirilo,
Hernandez Gilberto,
Biba Mirlinda,
Welch Christopher J.
Publication year - 2005
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.20154
Subject(s) - chemistry , enantiomer , optical rotation , diastereomer , chloroform , composition (language) , enantiomeric excess , chirality (physics) , nuclear magnetic resonance spectroscopy , analytical chemistry (journal) , stereochemistry , chromatography , organic chemistry , enantioselective synthesis , chiral symmetry , catalysis , linguistics , philosophy , nambu–jona lasinio model , physics , quantum mechanics , quark
Partial resolution of rac ‐2‐ tert ‐butyltetrahydroimidazolidin‐4‐one was carried out by recrystallization of diastereomeric salts. The enantiomeric composition of enriched samples was estimated by polarimetry, 1 H NMR, and chiral SFC. Enantiomeric composition estimated by polarimetry or by 1 H NMR was directly proportional to that estimated by chiral SFC. The occurrence of solute self‐association in chloroform was detected through measurements of optical and specific rotation at variable concentration of (−)‐( R )‐2‐ tert ‐butyltetrahydroimidazolidin‐4‐one. Our data suggest that solute self‐association in chloroform might be independent of enantiomeric composition. Chirality 17:212–217, 2005. © 2005 Wiley‐Liss, Inc.