2.2.2-Cryptand

[2.2.2]Cryptand bracket omission [2.2.2]Cryptand changed 477215715 Cryptand.svg Skeletal formula of 2.2.2-cryptand 150 2.2.2-Cryptand-3D-balls-by-AHRLS-2012.png 150 2.2.2-Cryptand-3D-sticks-by-AHRLS-2012.png 140 2.2.2-Cryptand-3D-vdW-by-AHRLS-2012.png 140 4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane Cryptating agent 222In the Nomenclature of Inorganic Chemistry (2005), IUPAC recommends the abbreviation crypt-222. Crypt-222 23978-09-8 correct CAS correct FDA 18V22YHN6G 72801 65637 correct chemspider 245-962-4 Cryptating+agent+222 MP4750000 620282 C1COCCN2CCOCCOCCN(CCO1)CCOCCOCC2 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 correct chemspider 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 AUFVJZSDSXXFOI-UHFFFAOYSA-N correct chemspider AUFVJZSDSXXFOI-UHFFFAOYAX C 18 N 2 H 36 O 6 376.4882 g mol−1 68 to 71 exclamation mark WARNING 315 319 335 261 305+351+338 [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.Kang Sung Ok Llinares José M. Day Victor W. Bowman-James Kristin Kristin Bowman-James 2010 Cryptand-like anion receptors Chemical Society Reviews 39 10 3980–4003 10.1039/C0CS00083C 20820597 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,10.1016/S0040-4039(01)88300-3 Les Cryptates 1969 Dietrich B. Lehn J.M. Sauvage J.P. Tetrahedron Letters 10 34 2889–2892 Jean-Marie Lehn shared the Nobel Prize in Chemistry. The compound was originally prepared starting with the diacylation of the diamine-diether:10.1016/S0040-4039(01)88299-X Diaza-polyoxa-macrocycles et macrobicycles 1969 Dietrich B. Lehn J.M. Sauvage J.P. Tetrahedron Letters 10 34 2885–2888 [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. thumbnail|left|Structure of [2.2.2]cryptand encapsulating a potassium cation (purple) as determined by X-ray crystallographyAlberto, R. Ortner, K. Wheatley, N. Schibli, R. Schubiger, A. P. 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. 2001 121 3135–3136 10.1021/ja003932b 11457025 13 References Category:Chelating agents