Abstract
Chiral rccognition 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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