[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]
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.
^In the Nomenclature of Inorganic Chemistry (2005), IUPAC recommends the abbreviation crypt-222.
^Kang, Sung Ok; Llinares, José M.; Day, Victor W.; Bowman-James, Kristin (2010). "Cryptand-like anion receptors". Chemical Society Reviews. 39 (10): 3980–4003. doi:10.1039/C0CS00083C. PMID 20820597.
^Alberto, R.; Ortner, K.; Wheatley, N.; Schibli, R.; Schubiger, A. P. (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.121 (13): 3135–3136. doi:10.1021/ja003932b. PMID 11457025.
January 01, 1970
cryptand, correct, title, this, article, cryptand, omission, brackets, technical, restrictions, cryptand, organic, compound, with, formula, ch2ch2och2ch2och2ch2, this, bicyclic, molecule, most, studied, member, cryptand, family, chelating, agents, white, solid. The correct title of this article is 2 2 2 Cryptand The omission of any brackets is due to technical restrictions 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 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 1 Identifiers CAS Number 23978 09 8 Y 3D model JSmol Interactive image Abbreviations Crypt 222 Beilstein Reference 620282 ChemSpider 65637 Y ECHA InfoCard 100 041 770 EC Number 245 962 4 MeSH Cryptating agent 222 PubChem CID 72801 RTECS number MP4750000 UNII 18V22YHN6G Y CompTox Dashboard EPA DTXSID00178697 InChI 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 YKey AUFVJZSDSXXFOI UHFFFAOYSA N YInChI 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 18H2Key AUFVJZSDSXXFOI UHFFFAOYAX SMILES C1COCCN2CCOCCOCCN CCO1 CCOCCOCC2 Properties Chemical formula C18 N2 H36 O6 Molar mass 376 4882 g mol 1 Melting point 68 to 71 C 154 to 160 F 341 to 344 K Hazards GHS labelling Pictograms Signal word Warning Hazard statements H315 H319 H335 Precautionary statements 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 Y N Infobox references 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 Structure of 2 2 2 cryptand encapsulating a potassium cation purple as determined by X ray crystallography 5 References edit In the Nomenclature of Inorganic Chemistry 2005 IUPAC recommends the abbreviation crypt 222 Kang Sung Ok Llinares Jose M Day Victor W Bowman James Kristin 2010 Cryptand like anion receptors Chemical Society Reviews 39 10 3980 4003 doi 10 1039 C0CS00083C PMID 20820597 Dietrich B Lehn J M Sauvage J P 1969 Les Cryptates Tetrahedron Letters 10 34 2889 2892 doi 10 1016 S0040 4039 01 88300 3 Dietrich B Lehn J M Sauvage J P 1969 Diaza polyoxa macrocycles et macrobicycles Tetrahedron Letters 10 34 2885 2888 doi 10 1016 S0040 4039 01 88299 X Alberto R Ortner K Wheatley N Schibli R Schubiger A P 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 121 13 3135 3136 doi 10 1021 ja003932b PMID 11457025 Retrieved from https en wikipedia org w index php title 2 2 2 Cryptand amp oldid 1211033081, wikipedia, wiki, book, books, library,
