title: Supramolecular recognition and structural elucidation of inclusion complexes of an achiral carbene precursor in beta- and permethylated beta-cyclodextrin.
abstract: [structure: see text] Inclusion of achiral carbene precursor endo-8-azibicyclo[3.2.1]octan-3-ol (1) in chiral beta-cyclodextrin (7-Cy) and tri-O-methyl-beta-cyclodextrin (TRIMEB) leads to 1:1 complexes 1@7-Cy and 1@TRIMEB, respectively. The combined methods of induced circular dichroism, NMR spectroscopy, and X-ray structure determination were employed for the first time for structural elucidation of the complexes in solution and the solid state. Significantly different orientations of 1 were observed. Compared with 1@7-Cy, 1@TRIMEB exhibits a different guest orientation and an association constant one-twentieth lower.
authors.affiliation: Institut für Organische Chemie, Universität Wien, Währinger Strasse 38, A-1090 Wien, Austria.
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Mieusset
authors.forename: Daniel
authors.initials: D
authors.lastname: Krois
authors.forename: Mirjana
authors.initials: M
authors.lastname: Pacar
authors.forename: Lothar
authors.initials: L
authors.lastname: Brecker
authors.forename: Gerald
authors.initials: G
authors.lastname: Giester
authors.forename: Udo H
authors.initials: UH
authors.lastname: Brinker
mesh_terms: D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D006838:Hydrocarbons; D047392:beta-Cyclodextrins; C030011:carbene; D008697:Methane