Application of L-proline derivatives as chiral shift reagents for enantiomeric recognition of carboxylic acids


Naziroglu H. N., Durmaz M., BOZKURT S., Sirit A.

Chirality, cilt.23, sa.6, ss.463-471, 2011 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 23 Sayı: 6
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1002/chir.20948
  • Dergi Adı: Chirality
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.463-471
  • Anahtar Kelimeler: carboxylic acid, chiral recognition, enantiomeric excess, L -proline, NMR titration
  • Uşak Üniversitesi Adresli: Evet

Özet

Four proline-derived chiral receptors 5-8 were readily synthesized starting from L-proline. The enantiomeric recognition ability of chiral receptors was examined with a series of carboxylic acids by 1H NMR spectroscopy. The molar ratio and the association constants of the chiral compounds with each of the enantiomers of guest molecules were determined by using Job plots and a nonlinear least-squares fitting method, respectively. The Job plots indicate that the hosts form 1:1 instantaneous complexes with all guests. The receptors exhibited different chiral recognition abilities toward the enantiomers of racemic guests. Among the chiral receptors used in this study, prolinamide 6 was found to be the best chiral shift reagent and is effective for the determination of the enantiomeric excess of chiral carboxylic acids. Copyright © 2011 Wiley-Liss, Inc.