Recent Advances in Multinuclear NMR Spectroscopy for Chiral Recognition of Organic Compounds

Molecules. 2017 Feb 7;22(2):247. doi: 10.3390/molecules22020247.

Abstract

Nuclear magnetic resonance (NMR) is a powerful tool for the elucidation of chemical structure and chiral recognition. In the last decade, the number of probes, media, and experiments to analyze chiral environments has rapidly increased. The evaluation of chiral molecules and systems has become a routine task in almost all NMR laboratories, allowing for the determination of molecular connectivities and the construction of spatial relationships. Among the features that improve the chiral recognition abilities by NMR is the application of different nuclei. The simplicity of the multinuclear NMR spectra relative to ¹H, the minimal influence of the experimental conditions, and the larger shift dispersion make these nuclei especially suitable for NMR analysis. Herein, the recent advances in multinuclear (19F, 31P, 13C, and 77Se) NMR spectroscopy for chiral recognition of organic compounds are presented. The review describes new chiral derivatizing agents and chiral solvating agents used for stereodiscrimination and the assignment of the absolute configuration of small organic compounds.

Keywords: NMR spectroscopy; absolute configuration; chiral recognition; chirality; enantiomeric excess; enantiopurity; multinuclear; stereochemistry.

Publication types

  • Review

MeSH terms

  • Carboxylic Acids / chemistry
  • Coordination Complexes / chemistry
  • Cyclodextrins / chemistry
  • Ionic Liquids / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Nuclear Magnetic Resonance, Biomolecular / methods*
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Carboxylic Acids
  • Coordination Complexes
  • Cyclodextrins
  • Ionic Liquids
  • Palladium