Enantiomeric recognition of α-(1-naphthyl)ethylammonium perchlorate by enantiomerically pure dimethylphenazino-18-crown-6 ligand in solid and gas phases

Tímea Gérczei, Zsolt Böcskei, György M. Keseru, Erika Samu, Péter Huszthy

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

X-Ray crystallographic studies of enantiomerically pure dimethylphenazino-18-crown-6 ligand (R,R)-1 and its complexes with the enantiomers of α-(1-naphthyl)ethylammonium perchlorate NapEt were carried out. These studies clearly show that the heterochiral complex (R,R)-1-(S)- NapEt is more stable than the homochiral one (R,R)-1-(R)-NapEt. It was pointed out that besides the hydrogen bonding, mainly the π-π interaction between the aromatic systems of the host and guest, and the difference in steric repulsions were responsible for enantioselectivity. Molecular mechanical calculations using the LMOD/MINTA method also predicted the heterochiral complex to be more stable than the homochiral one in the gas phase.

Original languageEnglish
Pages (from-to)1995-2005
Number of pages11
JournalTetrahedron Asymmetry
Volume10
Issue number10
DOIs
Publication statusPublished - May 21 1999

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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