18-Crown-6

18-Crown-6 is an organic compound with the formula [C2H4O]6 and the IUPAC name of 1,4,7,10,13,16-hexaoxacyclooctadecane. It is a white, hygroscopic crystalline solid with a low melting point. Like other crown ethers, 18-crown-6 functions as a ligand for some metal cations with a particular affinity for potassium cations (binding constant in methanol: 106 M−1). The point group of 18-crown-6 is S6. The dipole moment of 18-crown-6 varies in different solvent and under different temperature. Under 25 °C, the dipole moment of 18-crown-6 is 2.76 ± 0.06 D in cyclohexane and 2.73 ± 0.02 in benzene. The synthesis of the crown ethers led to the awarding of the Nobel Prize in Chemistry to Charles J. Pedersen.

See also: Dibenzo-18-crown-6
18-Crown-6
Names
Preferred IUPAC name
1,4,7,10,13,16-Hexaoxacyclooctadecane
Identifiers
3D model (JSmol)
1619616
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.037.687
EC Number
  • 241-473-5
4535
PubChem CID
UNII
  • InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2 Y
    Key: XEZNGIUYQVAUSS-UHFFFAOYSA-N Y
  • 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
SMILES
  • O1CCOCCOCCOCCOCCOCC1
  • C1COCCOCCOCCOCCOCCO1
Properties
C12H24O6
Molar mass 264.315 g/mol
Density 1.237 g/cm3
Melting point 37 to 40 °C (99 to 104 °F; 310 to 313 K)
Boiling point 116 °C (241 °F; 389 K) (0.2 Torr)
75 g/L
Hazards
GHS labelling:
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds
 Dibenzo-18-crown-6
Triglyme
Hexaaza-18-crown-6
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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