A direct chromatographic separation of enantiomers chiral by virtue of isotopic substitution

✍ Scribed by William H. Pirkle; Kevin Z. Gan

• Book ID: 104361065
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 227 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00037-2

✦ Synopsis

An unprecedented isotope effect on rr-rr face to edge interaction was observed in the separations of the enantiomers of the pivalamide of e(,od-phenyl-(phenyl-d5)methylamine 3a, and the p,p' disubstituted analogs on CSP 2. The configuration of the more retained enantiomer of its p,p'-dibromo derivative is assigned as R through dynamic NMR studies of a mixture of enantiomerically enriched sample of this compound and the chiral selector. The protonated aromatic group is more strongly held in the binding cleft of the chiral selector than is the deuterated aromatic group.