Chiral Recognition of Carboxylate Anions by (R)-BINOL-Based Macrocyclic Receptors

Molecules. 2019 Jul 19;24(14):2635. doi: 10.3390/molecules24142635.

Abstract

Three (R)-BINOL-based macrocyclic receptors obtained via double-amidation reaction were used for chiral recognition of four anions derived from α-hydroxy and α-amino acids. The structural factors of hosts and guests that affect chiral recognition processes were also investigated, indicating that the proper geometry of both receptor and guest molecules plays a crucial role in effective enantio-discrimination.

Keywords: BINOL; chiral anions; chiral recognition; coalescence; macrocyclic receptors.

MeSH terms

  • Anions / chemistry*
  • Carboxylic Acids / chemistry*
  • Cyclization
  • Hydrogen Bonding
  • Macrocyclic Compounds / chemistry*
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Spectrum Analysis

Substances

  • Anions
  • Carboxylic Acids
  • Macrocyclic Compounds
  • Naphthalenes
  • S(-)2,2'-dihydroxy-1,1'-binaphthyl