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|Title:||Enantioselective guest exchange in a chiral resorcinarenes cavity||Authors:||Botta, B
DELLE MONACHE, G
|Issue Date:||2002||Project:||None||Journal:||JOURNAL OF THE AMERICAN CHEMICAL SOCIETY||Abstract:||
Gas-phase proton-bound complexes between a chiral resorcinarene and some representative amino acids, that is, L- and D-alanine or L- and D-serine, were generated in the source of a Fourier transform ion cyclotron resonance mass spectrometer. Gas-phase exchange of the amino acid from the diastereomeric complexes with the enantiomers of 2-butylamine exhibits a significant enantioselectivity, which depends not only upon the configuration of the leaving guest but also on that of the incoming amine. These findings, coupled with molecular dynamic calculations, point to the observed gas-phase enantioselectivity as determined by the effects of the resorcinarene chiral cavity upon the diastereomeric exchange transition structures.
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