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.

[2.2.2]Cryptand
Names
Preferred IUPAC name
4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane
Other names
Cryptating agent 222
Identifiers
3D model (JSmol)
Abbreviations Crypt-222
620282
ChemSpider
ECHA InfoCard 100.041.770
EC Number
  • 245-962-4
MeSH Cryptating+agent+222
PubChem CID
RTECS number
  • MP4750000
UNII
  • 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/h1-18H2 Y
    Key: AUFVJZSDSXXFOI-UHFFFAOYSA-N Y
  • 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/h1-18H2
    Key: AUFVJZSDSXXFOI-UHFFFAOYAX
SMILES
  • C1COCCN2CCOCCOCCN(CCO1)CCOCCOCC2
Properties
C
18N
2H
36O
6
Molar mass 376.4882 g mol−1
Melting point 68 to 71 °C (154 to 160 °F; 341 to 344 K)
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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.

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