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.
Ball-and-stick model of the bis(12-crown-4)lithium cation
Like other crown ethers, 12-crown-4 complexes with alkali metal cations. The cavity diameter of 1.2-1.5 Å gives it a high selectivity towards the lithium cation (ionic diameter 1.36 Å)[2]
Its point group is S4. The dipole moment of 12-crown-4 varies with solvent and temperature. At 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.[3]
References
^Cook, Fred L.; Caruso, Thomas C.; Byrne, Michael P.; Bowers, Chauncey W.; Speck, Don H.; Liotta, Charles L. (1974). "Facile syntheses of 12-crown-4 and 15-crown-5". Tetrahedron Letters. 15 (46): 4029–4032. doi:10.1016/S0040-4039(01)92075-1.
^ abLiotta, Charles L.; Berkner, Joachim (2001), "12-Crown-4", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289X.rc262, ISBN978-0-471-93623-7
^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
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