A New Cryptand:  Synthesis and Complexation with Paraquat

Inspired by folded, nonpseudorotaxane complexes of bis(m-phenylene)-32-crown-10 systems, we synthesized a new bicyclic crown ether containing two 1,3,5-phenylene units linked by three tetra(ethyleneoxy) units. The new cryptand forms a “pseudorotaxane-like” inclusion complex with N,N‘-dimethyl-4,4‘-b...

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Bibliographic Details
Published in:Organic letters 1999-10, Vol.1 (7), p.1001-1004
Main Authors: Bryant, William S, Jones, Jason W, Mason, Philip E, Guzei, Ilia, Rheingold, Arnold L, Fronczek, Frank R, Nagvekar, Devdatt S, Gibson, Harry W
Format: Article
Language:English
Subjects:
Ethers, Cyclic - chemical synthesis
Ethers, Cyclic - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Paraquat - chemistry
Spectrometry, Mass, Fast Atom Bombardment
X-Ray Diffraction
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Summary:Inspired by folded, nonpseudorotaxane complexes of bis(m-phenylene)-32-crown-10 systems, we synthesized a new bicyclic crown ether containing two 1,3,5-phenylene units linked by three tetra(ethyleneoxy) units. The new cryptand forms a “pseudorotaxane-like” inclusion complex with N,N‘-dimethyl-4,4‘-bipyridinium bis(hexafluorophosphate) with association constant K a = 6.1 × 104 M-1, 100-fold greater than that of an analogous simple crown ether.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990780k