The discovery of crown ethers.
نویسنده
چکیده
The discovery of the crown ethers stemmed from efforts to control the catalytic activity of vanadium and copper by complexation with multidentate ligands. The first crown ether, 2,3,11,12-dibenzo-1,4,7,10,13,16-hexaoxacyclo-octadeca-2,11-diene, was obtained in 0.4% yield during an attempt to prepare a phenolic ligand from catechol and bis(2-chloroethyl)ether. This compound, which complexed with the sodium cation, was the first compound known to display such activity and became known as dibenzo-18-crown-6, an 18-atom heterocycle containing 6 oxygen atoms. Some 60 related compounds were made involving heterocyclic rings containing 12 to 60 atoms including 4 and 10 oxygen atoms. There are optimum polyether ring sizes for the different alkali metal cations: 15 to 18 for sodium, 18 for potassium, and 18 to 21 for cesium. Complexes having polyether to cation ratios of 1:1, 3:2, and 2:1 were prepared. Solubilization of inorganic salts in aprotic solvents, especially by saturated crown ethers, was demonstrated.
منابع مشابه
Polarographic Study of the Interactions between Thallium and Lead Ions and Some Crown Ethers in 90% Acetonitrile and 90% Ethanol Solutions
The complexation reactions between Tl+ and Pb2+ ions and crown ethers 12-crown-4(12C4), 15-crown-5 (15C5), benzo-15-crown-5 (B15C5), 18-crown-6 (18C6), dicyclohexyl-18-crown-6 (DC18C6) and aza-18-crown-6 (A18C6) were studied in 90% acetonitrile and 90% ethanol solutions at 25 °C, using an a.c. polarographic technique. The stoichiometry and stability of the complexes we...
متن کاملComplexation of Hydronium Ion with Several Crown Ethers in Nitromethane Solution
The interaction between hydronium ion and several crown ethers was studied via conductometry in nitromethane at 25 °C and 1H-NMR techniques. The stabilities of the resulting 1:1 complexes were determined from the conductance data and found to vary in the order DC18C6 > 18C6 > DB30C10 > DB24C8 > DB18C6 > ~B15C5 > DB21C7. For the first time, evidences for the formation of a 2:1 san...
متن کاملLiquid crystalline crown ethers.
In this chapter, a comprehensive review over the entire reserarch on liquid crystalline crown ethers since their discovery will be given. Monomeric and polymeric molecules containing crown ethers as well as aza crown ethers, thia crown ethers and crown ethers with several different heteroatoms will be presented. Liquid crystallinity is, in most cases, caused by the substituents attached to the ...
متن کاملSpectrophotometric Study of the Intreaction of some Benzo, Benzyl and Phnylcrown Ethers with Pi-Acceptor DDQ in Chloroform Solution
The interaction between benzo-15-crown-5 (B15C5), dibenzo-18-crown-6 (DB18C6), dibenzyl-daza-18crown-6 (DBzDA18C6), N-phenyl-aza-15-crown-5 (NPhA15C5) and dibenzopyridine-18-crown-6 (DBPy18C6) with π-acceptor 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in chloroform solution was studied spectrophotometrically. The interaction of B15C5-DDQ and DB18C6-DDQ caused the formation...
متن کاملPedersen C J. Cyclic polyethers and their complexes with metal salts. J. Amer. Chem. Soc. 89:7017-36. 1967
• The discovery of the first crown ether is described. Forty-seven other aromatic and saturated polyethers were synthesized and their properties determined. Many form stable crystalline complexes with alkali and alkaline earth salts. Some saturated crown ethers solubilize potassium hydroxide and permanganate in aromatic hydrocarbons, EThe SC!5 indicates that this paper has been cited in over 1,...
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ورودعنوان ژورنال:
- Science
دوره 241 4865 شماره
صفحات -
تاریخ انتشار 1988