12-Crown-4

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12-Crown-4
Skeletal formula of 12-crown-4
Ball-and-stick model of the 12-Crown-4 molecule
Names
IUPAC name
1,4,7,10-tetraoxacyclododecane
Other names
12-crown-4, Lithium Ionophore V
Identifiers
3D model (JSmol)
1363064
ChEBI
ChemSpider
ECHA InfoCard 100.005.488
EC Number 206-036-5
3287
UNII
Properties
C8H16O4
Molar mass 176.21
Density 1.089 g/mL at 25 °C
Melting point 16 °C
Boiling point 61-70 °C/0.5 mm Hg
Miscible
Hazards
no hazard statements
no precautionary statements
Flash point 113 °C (235 °F; 386 K)
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

12-Crown-4, also called 1,4,7,10-tetraoxacyclododecane and lithium ionophore V, is a crown ether with the formula C8H16O4. It is a cyclic tetramer of ethylene oxide which is specific for the lithium cation. Its point group is S4. The dipole moment of 12-crown-4 varies in different solvent and under different temperature. Under 25 °C, the dipole moment of 12-crown-4 was determined as 2.33 ± 0.03 D in cyclohexane and 2.46 ± 0.01 D in benzene.[1]

Ball-and-stick model of the bis(12-crown-4)lithium cation

References[edit]

  1. ^ Caswell, Lyman R.; Savannunt, Diana S. (January 1988). "Temperature and solvent effects on the experimental dipole moments of three crown ethers". Journal of Heterocyclic Chemistry. 25 (1): 73–79. doi:10.1002/jhet.5570250111. 
  • Sigma-Aldrich Handbook of Fine Chemicals, 2007, page 768.
  • Sigma-Aldrich Cyclic tetramer of ethylene oxide which is specific for the lithium cation. 98%, 2018

See also[edit]

  • Crown ether
  • Cyclen, a similar molecule with N atoms (aza groups) instead of O atoms (ethers)