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2.2.2-Cryptand

[2.2.2]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 [2.2.2]cryptand, Jean-Marie Lehn shared the Nobel Prize in Chemistry. The compound was originally prepared starting with the diacylation of the diamine-diether: :[CH2OCH2CH2NH2]2 + [CH2OCH2COCl]2 → [CH2OCH2CH2NHC(O)CH2]2 + 2 HCl The resulting macrocyclic diamide is reduced by lithium aluminium hydride. The resulting macrocyclic diamine tetraether reacts with a second equivalent of [CH2OCH2COCl]2 to produce the macrobicyclic diamide. This di(tertiary)amide is reduced to the diamine by diborane.

[2.2.2]Cryptand binds K+ as an octadentate N2O6 ligand. The resulting cation K([2.2.2]cryptand)+ is lipophilic.

References

References

  1. In the Nomenclature of Inorganic Chemistry (2005), IUPAC recommends the abbreviation crypt-222.
  2. (2010). "Cryptand-like anion receptors". Chemical Society Reviews.
  3. (1969). "Les Cryptates". Tetrahedron Letters.
  4. (1969). "Diaza-polyoxa-macrocycles et macrobicycles". Tetrahedron Letters.
  5. (2001). "Synthesis and properties of boranocarbonate: a convenient in situ CO source for the aqueous preparation of [99mTc(OH2)3(CO)3]+". [[J. Am. Chem. Soc.]].
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