2.2.2-Cryptand

[2.2.2]Cryptand is the <a href="/facts/Organic_compound/gqCNaN45">organic compound</a> with the formula N(CH2CH2OCH2CH2OCH2CH2)3N. This <a href="/facts/Cyclic_molecule/TH2ReKIQ">bicyclic</a> molecule is the most studied member of the <a href="/facts/Cryptand/H9Q2CetP">cryptand</a> family of <a href="/facts/Chelating_agent/4G79sXBB">chelating agents</a>. It is a white solid. Many analogous compounds are known. Their high affinity for <a href="/facts/Alkali_metal/IkWbCLk2">alkali metal</a> cations illustrates the advantages of "preorganization", a concept within the area of <a href="/facts/Supramolecular_chemistry/wwUfD0fk">supramolecular chemistry</a>. 
For the design and synthesis of [2.2.2]cryptand, <a href="/facts/Jean-Marie_Lehn/5AKDlGbE">Jean-Marie Lehn</a> shared the <a href="/facts/Nobel_Prize_in_Chemistry/8Nb8Ajjy">Nobel Prize in Chemistry</a>. 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 <a href="/facts/Macrocycle/4GPougjf">macrocyclic</a> diamide is reduced by <a href="/facts/Lithium_aluminium_hydride/QMMhdqEy">lithium aluminium hydride</a>. 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 <a href="/facts/Diborane/k7egwbPf">diborane</a>.
[2.2.2]Cryptand binds <a href="/facts/Potassium/FWPwS7Rj">K+</a> as an <a href="/facts/Denticity/hJF1lAJz">octadentate</a> N2O6 ligand. The resulting cation K([2.2.2]cryptand)+ is lipophilic.

2.2.2-Cryptand open-in-new

2.2.2-Cryptand