A new cryptand: synthesis and complexation with paraquat

W S Bryant; J W Jones; P E Mason; I Guzei; A L Rheingold; F R Fronczek; D S Nagvekar; H W Gibson

doi:10.1021/ol990780k

A new cryptand: synthesis and complexation with paraquat

Org Lett. 1999 Oct 7;1(7):1001-4. doi: 10.1021/ol990780k.

Authors

W S Bryant¹, J W Jones, P E Mason, I Guzei, A L Rheingold, F R Fronczek, D S Nagvekar, H W Gibson

Affiliation

¹ Department of Chemistry, Virginia Polytechnic Institute & State University, Blacksburg 24061, USA.

PMID: 10825952
DOI: 10.1021/ol990780k

Abstract

[formula: see text] 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 Ka = 6.1 x 10(4) M-1, 100-fold greater than that of an analogous simple crown ether.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Ethers, Cyclic / chemical synthesis*
Ethers, Cyclic / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Paraquat / chemistry*
Spectrometry, Mass, Fast Atom Bombardment
X-Ray Diffraction

Substances

Ethers, Cyclic
Paraquat

Grants and funding

P41RR0954/RR/NCRR NIH HHS/United States