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The interaction of inherently chiral resorc[4]arenes with different chiral ammonium ions was measured by ESI-MS. For that purpose one enantiomer of the ammonium guests was labeled with deuterium to distinguish the enantiomers by their mass. We synthesized the ammonium salts by reaction of chiral primary amines with either CH3I or CD3I and analyzed the resulting ammonium iodides by NMR and optical rotation. The complexation experiments were performed by mixing the chiral host with various ratios of the unlabeled guest and its labeled enantiomer. By analysis of the integrals of the host-guest complexes we observed a chiral discrimination effect and a secondary isotope effect as well.
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Mehdizadeh et al. (2004) studied this question.