Molecular clips based on propanediurea. Exceptionally high binding affinities for resorcinol guests

Jansen, Rob J., de Gelder, Rene, Rowan, Alan E., Scheeren, Hans W. and Nolte, Roeland J. M. (2001) Molecular clips based on propanediurea. Exceptionally high binding affinities for resorcinol guests. Journal of Organic Chemistry, 66 8: 2643-2653. doi:10.1021/jo001317k


Author Jansen, Rob J.
de Gelder, Rene
Rowan, Alan E.
Scheeren, Hans W.
Nolte, Roeland J. M.
Title Molecular clips based on propanediurea. Exceptionally high binding affinities for resorcinol guests
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
1520-6904
Publication date 2001-04-01
Year available 2001
Sub-type Article (original research)
DOI 10.1021/jo001317k
Open Access Status Not yet assessed
Volume 66
Issue 8
Start page 2643
End page 2653
Total pages 11
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Abstract A series of new receptor molecules derived from 2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione (propanediurea) is described. These molecules possess a cavity which is defined by two nearly parallel aromatic side walls positioned on top of a bis-urea framework. The resulting “U-shaped” clip molecules are ideal hosts for the complexation of flat aromatic guest molecules. The affinity of these new propanediurea based molecular clips for dihydroxybenzene derivatives is exceptionally high, with association constants up to Ka = 2 400 000 L mol-1. Comparison of the binding mechanism of a variety of clip and half clip hosts, in conjunction with NMR, IR, and X-ray studies, has enabled the reason for this high binding to be elucidated. It is shown that subtle sub-angstrom changes in the geometry of the clip molecules have a great impact on their binding properties.
Keyword Chemistry, Organic
Chemistry
CHEMISTRY, ORGANIC
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Australian Institute for Bioengineering and Nanotechnology Publications
 
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