title: Macrocyclic chiral receptors toward enantioselective recognition of naproxen.
abstract: [structure: see text] A macrocyclic receptor based on a bischromenylurea and an alpha,alpha'-(o,o'-dialkyl)diphenyl-p-xylylenediamine spacer provides a C(2) chiral cavity to associate carboxylates by H-bonds. The extent of the selectivity obtained for the racemic receptor 2 and enantiomerically pure (S)-naproxen is 7.2:1. Steric repulsions close to the cavity are decisive for the chiral selectivity.
authors.affiliation: Departamento de Química Organica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain.
authors.forename: Silvia
authors.initials: S
authors.lastname: Gonzalez
authors.forename: Rafael
authors.initials: R
authors.lastname: Pelaez
authors.forename: Francisca
authors.initials: F
authors.lastname: Sanz
authors.forename: M Belén
authors.initials: MB
authors.lastname: Jiménez
authors.forename: Joaquín R
authors.initials: JR
authors.lastname: Moran
authors.forename: M Cruz
authors.initials: MC
authors.lastname: Caballero
mesh_terms: D001665:Binding Sites; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D009288:Naproxen / Q000737:chemistry*; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry*; D014992:Xylenes / Q000737:chemistry*
chemical_list: D014992:Xylenes; D009288:Naproxen; D014508:Urea