Synthesis of chiral crown ethers and complexation with chiral protonated amine compounds: X-ray crystal and nuclear magnetic resonance studies of perchlorate salt of chiral benzo-monoaza-15-crown-5 and chiral monoaza-15-crown-5


TOGRUL M., DEMIREL N., KAYNAK F. B. , Ozbey S., HOSGOREN H.

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, vol.50, pp.165-171, 2004 (Peer-Reviewed Journal) identifier

  • Publication Type: Article / Article
  • Volume: 50
  • Publication Date: 2004
  • Journal Name: JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.165-171

Abstract

The X-ray crystal structure of IX, perchlorate salt of R-(-)-2-ethyl-N-benzyl-4,7,19,13-tetraoxa-8,9-benzo-1-azacyclopentadec-8-ene has been determined. In the molecule, the protonated nitrogen atom participates in two N-(HO)-O-... hydrogen bonds. The unusually high proton affinity of aza crown ether leads to the formation of diastreomer instead of complex formation with chiral R-(+)-1-phenyl ethyl ammonium perchlorate and S-(-)-1-phenyl ethyl ammonium perchlorate. The complex ability of host ethers was evaluated in terms of structural modification.