10241. Cryptand 222

Nomenclature

CAS number: 23978-09-8
4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane; Kryptofix 222 (Merck KGaA).
C18H36N2O6; mol wt 376.49.
C 57.42%, H 9.64%, N 7.44%, O 25.50%.

Description and references

Macrocyclic ligand; sequestering agent for metal ions in solution. Prepn: B. Dietrich et al., Tetrahedron 29, 1629 (1973) DOI. Synthesis of complexes with metal ions: A. Knchel et al., Inorg. Nucl. Chem. Lett. 11, 787 (1975) DOI. Crystal structure: B. Metz et al., J. Chem. Soc. Perkin Trans. 2 1976, 423 DOI. Thermodynamic properties in water and methanol: M. H. Abraham et al., J. Chem. Soc. Faraday Trans. 1 76, 869 (1980) DOI. Adsorption properties: M. Carlà et al., J. Phys. Chem. 100, 11067 (1996) DOI. Solution properties: P. Jost et al., Phys. Chem. Chem. Phys. 4, 335 (2002) DOI. Review of thermodynamic properties: Y. Marcus, Rev. Anal. Chem. 23, 269-302 (2004).

Chemical structure

Properties

Crystals from hexane, mp 68-69°. d 1.07 ±0.02. Very sol in water. Soly at 25° in cyclohexane: 0.238 M; in tetradecane: 0.086 M. Partition coefficient (cyclohexane/water): 0.0249. Partition coefficient (tetradecane/water): 0.0129. Irritant.

Use

In selective complexing and membrane transport of cations, metal purification procedures, phase transfer catalysis, anionic polymerizations, solubilization of insoluble salts in low polarity solvents.