A new cryptand: synthesis and complexation with paraquat.
[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.
Bryant
W S
WS
Department of Chemistry, Virginia Polytechnic Institute & State University, Blacksburg 24061, USA.
Jones
J W
JW
Mason
P E
PE
Guzei
I
I
Rheingold
A L
AL
Fronczek
F R
FR
Nagvekar
D S
DS
Gibson
H W
HW
D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010269:Paraquat / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014961:X-Ray Diffraction
D004988:Ethers, Cyclic; D010269:Paraquat