Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/4665
Title: Enantioselective guest exchange in a chiral resorcin[4]arenes cavity
Authors: Botta, B
Botta, Maurizio 
Filippi, A
Tafi, Andrea 
DELLE MONACHE, G
Speranza, M.
Issue Date: 2002
Project: None 
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Abstract: 
Gas-phase proton-bound complexes between a chiral resorcin[4]arene 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 resorcin[4]arene chiral cavity upon the diastereomeric exchange transition structures.
Description: 
37610
URI: http://hdl.handle.net/20.500.12779/4665
ISSN: 0002-7863
DOI: 10.1021/ja020232t
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