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Crown ether
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==History== In 1967, [[Charles Pedersen]], who was a [[chemist]] working at [[DuPont]], discovered a simple method of synthesizing a crown ether when he was trying to prepare a [[complexing agent]] for [[divalent cation]]s.<ref>{{Cite journal| last1 = Pedersen | first1 = C. J.| title = Cyclic polyethers and their complexes with metal salts| journal = Journal of the American Chemical Society| volume = 89| issue = 26| pages = 7017β7036| year = 1967 | doi = 10.1021/ja01002a035| bibcode = 1967JAChS..89.7017P}}</ref><ref>{{Cite journal| last1 = Pedersen | first1 = C. J.| title = Cyclic polyethers and their complexes with metal salts| journal = Journal of the American Chemical Society| volume = 89| issue = 10| pages = 2495β2496| year = 1967 | doi = 10.1021/ja00986a052| bibcode = 1967JAChS..89.2495P}}</ref> His strategy entailed linking two [[catechol]]ate groups through one [[hydroxyl]] on each molecule. This linking defines a polydentate ligand that could partially envelop the cation and, by [[ionization]] of the phenolic hydroxyls, neutralize the bound dication. He was surprised to isolate a [[by-product]] that strongly complexed [[potassium]] cations. Citing earlier work on the dissolution of [[potassium]] in 16-crown-4,<ref name="stewart">{{cite patent|inventor1-first=D. G.|inventor1-last=Stewart|inventor2-first= D. Y. |inventor2-last=Waddan |inventor3-first=E. T. |inventor3-last=Borrows |country-code=GB|patent-number=785229|issue-date= 1957-10-23}}</ref><ref name="down">{{cite journal|last1=Down|first1=J. L.|last2=Lewis|first2=J.|last3=Moore|first3=B.|last4=Wilkinson|first4=G.|title=761. The solubility of alkali metals in ethers|journal=Journal of the Chemical Society |year=1959|pages=3767 |doi=10.1039/jr9590003767}}</ref> he realized that the cyclic [[polyether]]s represented a new class of complexing agents that were capable of binding [[alkali metal]] cations. He proceeded to report systematic studies of the synthesis and binding properties of crown ethers in a seminal series of papers. The fields of [[organic synthesis]], [[phase transfer catalyst]]s, and other emerging disciplines benefited from the discovery of crown ethers. Pedersen particularly popularized the dibenzo crown ethers.<ref>{{OrgSynth | first= Charles J.|last= Pedersen | title = Macrocyclic Polyethers: Dibenzo-18-Crown-6 Polyether and Dicyclohexyl-18-Crown-6 Polyether | collvol = 6 | collvolpages = 395 | year = 1988 | prep = CV6P0395}}</ref> Pedersen shared the 1987 [[Nobel Prize in Chemistry]] for the discovery of the synthetic routes to, and binding properties of, crown ethers.
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