2.2.2-Cryptand

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Template:Correct title <templatestyles src="Chembox/styles.css"/>

Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox GHS (set)Template:Chembox Datapage checkTemplate:Chembox Footer
[2.2.2]Cryptand
Template:Chembox image sbs cell
Template:Longitem Template:Unbulleted list
Abbreviations Crypt-222
Template:Longitem 620282
ChEBI Template:Unbulleted list
ChemSpider Template:Unbulleted list
DrugBank Template:Unbulleted list
EC Number Template:Unbulleted list
KEGG Template:Unbulleted list
MeSH Cryptating+agent+222
Template:Longitem Template:Unbulleted list
RTECS number Template:Unbulleted list
Script error: No such module "collapsible list".
Script error: No such module "collapsible list".
Template:Longitem Template:Chem/link
Molar mass 376.4882 g mol−1
Melting point Template:Chembox CalcTemperatures

Template:Chembox Footer/trackingScript error: No such module "TemplatePar".Template:Short description

[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.[2] 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,[3] Jean-Marie Lehn shared the Nobel Prize in Chemistry. The compound was originally prepared starting with the diacylation of the diamine-diether:[4]

[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.

File:Cryptate of potassium cation.jpg
Structure of [2.2.2]cryptand encapsulating a potassium cation (purple) as determined by X-ray crystallography[5]

References

<templatestyles src="Reflist/styles.css" />

  1. ↑ In the Nomenclature of Inorganic Chemistry (2005), IUPAC recommends the abbreviation crypt-222.
  2. ↑ Script error: No such module "Citation/CS1".
  3. ↑ Script error: No such module "Citation/CS1".
  4. ↑ Script error: No such module "Citation/CS1".
  5. ↑ Script error: No such module "Citation/CS1".

Script error: No such module "Check for unknown parameters".

Retrieved from "http://debianws.lexgopc.com/wiki143/index.php?title=2.2.2-Cryptand&oldid=7175142"