Chiral Host-Guest Recognition in the Solvent Free Gas Phase as Determined by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR/MS)

Abstract

Chiral recognition is observed for a gas-phase host-guest system by using Fourier transform ion cyclotron resonance mass spectrometry to determine equilibrium constants for the transfer of R-or S-(1-naphthyl)ethylammonium (NapEt+) cation from S,S-dimethyldiketopyridino-18-crown-6 to unsubstituted 18- crown-6. The unsubstituted crown has substantially higher affinity for both guests than the chiral crown. The measured equilibrium constants are 130 +/- 15 for R-NapEt+, and 567 +/- 68 for S-NapEt+, yielding a difference of 4.2 +/- 0.4 kJ/mol-1 between the stabilities of the complexes of the two enantiomeric guests with the chiral host.

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Document Details

Document Type
Technical Report
Publication Date
Mar 17, 1993
Accession Number
ADA262196

Entities

People

  • D. V. Dearden
  • I.-h. Chu
  • J. S. Bradshaw
  • P. Huszthy
  • Reed Izatt

Organizations

  • Brigham Young University

Tags

DTIC Thesaurus Topics

  • Abstracts
  • Chemical Reaction Properties
  • Chemistry
  • Cyclotron Resonance
  • Cyclotrons
  • Enantiomers
  • Free Energy
  • Ions
  • Mass Spectra
  • Mass Spectrometry
  • Military Research
  • Reaction Time
  • Recognition
  • Resonance
  • Spectrometry
  • Spectroscopy
  • United States Government

Fields of Study

  • Chemistry

Readers

  • Molecular Photonics/Laser Physics
  • Organic Chemistry