Supramolecular Recognition and Structural Elucidation of Inclusion Complexes of an Achiral Carbene Precursor in β- and Permethylated β-Cyclodextrin

Inclusion of achiral carbene precursor endo-8-azibicyclo[3.2.1]octan-3-ol (1) in chiral β-cyclodextrin (7-Cy) and tri-O-methyl-β-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 d...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2004-06, Vol.6 (12), p.1967-1970
Main Authors: Mieusset, Jean-Luc, Krois, Daniel, Pacar, Mirjana, Brecker, Lothar, Giester, Gerald, Brinker, Udo H
Format: Article
Language:English
Subjects:
beta-Cyclodextrins - chemistry
Hydrocarbons
Methane - analogs & derivatives
Methane - chemistry
Models, Chemical
Molecular Structure
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Inclusion of achiral carbene precursor endo-8-azibicyclo[3.2.1]octan-3-ol (1) in chiral β-cyclodextrin (7-Cy) and tri-O-methyl-β-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049478o