18-crown -6

18-Crown-6
IUPAC name 1,4,7,10,13,16-hexaoxacyclooctadecane
Identification information
CAS registration number	17,455-13-9
PubChem	28557
ChemSpider	26563
It is an address number on a day	J49.431C
ChEMBL	CHEMBL155204
SMILES O1CCOCCOCCOCCOCCOCC1 C1COCCOCCOCCOCCOCCO1
InChI InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2  Key: XEZNGIUYQVAUSS-UHFFFAOYSA-N  InChI=1/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2 Key: XEZNGIUYQVAUSS-UHFFFAOYAP
Characteristic
Chemical formula	C12H24O6
Molar mass	264.122 g/mol
Density	1.237 g/cm³
Melting point	37-40 degrees Celsius
The boiling point	116 degrees Celsius (0.2 Torr)
Associated material
Related material	Dibenzo-18-crown -6 トリグライム
I can put a case, the data without the special mention for normal temperature (25 degrees Celsius), the ordinary pressure (100 kPa).

18-crown -6 (18-crown-6) is an organic compound expressed with molecular formula [C₂H₄O]₆, IUPAC name 1,4,7,10,13,16- hexaoxa cyclooctadecane. This compound is a kind of the crown ether. The crown ethers coordinate some metal cations in the central cavity. 18-crown -6 shows affinity for a potassium cation in particular. By an achievement of the development of crown ethers, Charles Pedersen won Nobel Prize in Chemistry of 1987.

Table of contents

Synthetic

I can prepare this compound by improved Williamson ether synthesis and [¹], oligomerizing internal of template cation existence lower ethylene oxide.

I can be refined by the distillation, and a tendency of becoming it becomes clear the supercooling of this compound then. 18-crown -6 can be refined by deposition with acetonitrile forming an insoluble complex again. Acetonitrile is removed under reduced pressure, and an objective compound is provided [¹]. By after the dry materials dissolved 18-crown -6 in THF closely, adding a sodium potassium alloy; [K(18-crown-6)] of the alkali salt Na is provided.

Applied

The crown ethers are useful as phase transfer catalysis [²]. An 18-crown -6 existence bottom, potassium permanganate dissolve in benzene. However, the use of the quaternary ammonium / phosphonium salt is superior for this purpose.

 

The potassium acetate becomes the stronger nucleophilic reagent in organic solvents when I use 18-crown -6.

Related compounds

Dibenzo-18-crown -6 is generally superior as complexing agent of the alkali metals cation.

 

Footnote

[Help]

1. ^ ^{a b} George W. Gokel, Donald J. Cram, Charles L. Liotta, Henry P. Harris, and Fred L. Cook (1988), "18-Crown-6," it is Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0301 Coll. Vol. 6: 301.
2. ^ Liotta, C. L.; Berknerin, J. "18-Crown-6" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi: 10.1002/047084289X.rc261

References

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Allied item

Wiki media Commons has a category in conjunction with 18-crown -6.

• Crown ether
• Cyclooctadecane

Outside link

• Sigma Aldrich chemical profile

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