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2.2.2-Cryptand

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The correct title of this article is Cryptand. The omission of any brackets is due to technical restrictions.
Cryptand
Skeletal formula of 2.2.2-cryptand
Names
Preferred IUPAC name 4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclohexacosane
Other names Cryptating agent 222
Identifiers
CAS Number
3D model (JSmol)
Abbreviations Crypt-222
Beilstein Reference 620282
ChemSpider
ECHA InfoCard 100.041.770 Edit this at Wikidata
EC Number
  • 245-962-4
MeSH Cryptating+agent+222
PubChem CID
RTECS number
  • MP4750000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H36N2O6/c1-7-21-13-14-24-10-4-20-5-11-25-17-15-22-8-2-19(1)3-9-23-16-18-26-12-6-20/h1-18H2Key: AUFVJZSDSXXFOI-UHFFFAOYSA-N
  • InChI=1/C18H36N2O6/c1-7-21-13-14-24-10-4-20-5-11-25-17-15-22-8-2-19(1)3-9-23-16-18-26-12-6-20/h1-18H2Key: AUFVJZSDSXXFOI-UHFFFAOYAX
SMILES
  • C1COCCN2CCOCCOCCN(CCO1)CCOCCOCC2
Properties
Chemical formula C
18N
2H
36O
6
Molar mass 376.4882 g mol
Melting point 68 to 71 °C (154 to 160 °F; 341 to 344 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cryptand is the organic compound with the formula N(CH2CH2OCH2CH2OCH2CH2)3N. This bicyclic molecule is the most studied member of the cryptand family of chelating agents. It is a white solid. Many analogous compounds are known. Their high affinity for alkali metal cations illustrates the advantages of "preorganization", a concept within the area of supramolecular chemistry.

For the design and synthesis of cryptand, Jean-Marie Lehn shared the Nobel Prize in Chemistry. The compound was originally prepared starting with the diacylation of the diamine-diether:

2 + 2 → 2 + 2 HCl

The resulting macrocyclic diamide is reduced by lithium aluminium hydride. The resulting macrocyclic diamine tetraether reacts with a second equivalent of 2 to produce the macrobicyclic diamide. This di(tertiary)amide is reduced to the diamine by diborane.

Cryptand binds K as an octadentate N2O6 ligand. The resulting cation K(cryptand) is lipophilic.

Structure of cryptand encapsulating a potassium cation (purple) as determined by X-ray crystallography

References

  1. In the Nomenclature of Inorganic Chemistry (2005), IUPAC recommends the abbreviation crypt-222.
  2. Kang, Sung Ok; Llinares, José M.; Day, Victor W.; Bowman-James, Kristin (2010). "Cryptand-like anion receptors". Chemical Society Reviews. 39 (10): 3980–4003. doi:10.1039/C0CS00083C. PMID 20820597.
  3. Dietrich, B.; Lehn, J.M.; Sauvage, J.P. (1969). "Les Cryptates". Tetrahedron Letters. 10 (34): 2889–2892. doi:10.1016/S0040-4039(01)88300-3.
  4. Dietrich, B.; Lehn, J.M.; Sauvage, J.P. (1969). "Diaza-polyoxa-macrocycles et macrobicycles". Tetrahedron Letters. 10 (34): 2885–2888. doi:10.1016/S0040-4039(01)88299-X.
  5. Alberto, R.; Ortner, K.; Wheatley, N.; Schibli, R.; Schubiger, A. P. (2001). "Synthesis and properties of boranocarbonate: a convenient in situ CO source for the aqueous preparation of ". J. Am. Chem. Soc. 121 (13): 3135–3136. doi:10.1021/ja003932b. PMID 11457025.
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