Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2.2.2-Cryptand: Difference between pages

{{correct title|[2.2.2]Cryptand|reason=bracket|edit=omission}}

| Name = [2.2.2]Cryptand

| Watchedfields = changed

| verifiedrevid = 477215715

| ImageFile = Cryptand.svg

| ImageSize = 150

| ImageFile1 = 2.2.2-Cryptand-3D-balls-by-AHRLS-2012.png

| ImageSize1 = 150

| ImageFileL2 = 2.2.2-Cryptand-3D-sticks-by-AHRLS-2012.png

| ImageSizeL2 = 140

| ImageFileR2 = 2.2.2-Cryptand-3D-vdW-by-AHRLS-2012.png

| ImageSizeR2 = 140

| PIN = 4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane

| OtherNames = Cryptating agent 222<ref>In the Nomenclature of Inorganic Chemistry (2005), IUPAC recommends the abbreviation crypt-222.</ref>

|Section1={{Chembox Identifiers

| Abbreviations = Crypt-222

| CASNo = 23978-09-8

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 18V22YHN6G

| PubChem = 72801

| ChemSpiderID = 65637

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 245-962-4

| MeSHName = Cryptating+agent+222

| RTECS = MP4750000

| Beilstein = 620282

| SMILES = C1COCCN2CCOCCOCCN(CCO1)CCOCCOCC2

| StdInChI = 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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

| StdInChIKey = AUFVJZSDSXXFOI-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = AUFVJZSDSXXFOI-UHFFFAOYAX

|Section2={{Chembox Properties

| Formula = {{Chem|C|18|N|2|H|36|O|6}}

| MolarMass = 376.4882 g&nbsp;mol⁻¹

| MeltingPtC = 68 to 71

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS exclamation mark}}

| GHSSignalWord = '''WARNING'''

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|305+351+338}}

'''[2.2.2]Cryptand''' is the [[organic compound]] with the formula N(CH₂CH₂OCH₂CH₂OCH₂CH₂)₃N. This [[Cyclic molecule|bicyclic]] molecule is the most studied member of the [[cryptand]] family of [[chelating agent]]s.<ref>{{cite journal|last1=Kang|first1=Sung Ok|last2=Llinares|first2=José M.|last3=Day|first3=Victor W.|last4=Bowman-James|first4=Kristin|author-link4=Kristin Bowman-James|year=2010|title=Cryptand-like anion receptors|journal=Chemical Society Reviews|volume=39|issue=10|pages=3980–4003|doi=10.1039/C0CS00083C|pmid=20820597}}</ref> 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,<ref>{{cite journal |doi=10.1016/S0040-4039(01)88300-3|title=Les Cryptates|year=1969|last1=Dietrich|first1=B.|last2=Lehn|first2=J.M.|last3=Sauvage|first3=J.P.|journal=Tetrahedron Letters|volume=10|issue=34|pages=2889–2892}}</ref> [[Jean-Marie Lehn]] shared the [[Nobel Prize in Chemistry]]. The compound was originally prepared starting with the diacylation of the diamine-diether:<ref>{{cite journal |doi=10.1016/S0040-4039(01)88299-X|title=Diaza-polyoxa-macrocycles et macrobicycles|year=1969|last1=Dietrich|first1=B.|last2=Lehn|first2=J.M.|last3=Sauvage|first3=J.P.|journal=Tetrahedron Letters|volume=10|issue=34|pages=2885–2888}}</ref>

:[CH₂OCH₂CH₂NH₂]₂ + [CH₂OCH₂COCl]₂ → [CH₂OCH₂CH₂NHC(O)CH₂]₂ + 2 HCl

The resulting [[Macrocycle|macrocyclic]] diamide is reduced by [[lithium aluminium hydride]]. The resulting macrocyclic diamine tetraether reacts with a second equivalent of [CH₂OCH₂COCl]₂ to produce the macro''bi''cyclic diamide. This di(tertiary)amide is reduced to the diamine by [[diborane]].

[2.2.2]Cryptand binds [[potassium|K⁺]] as an [[Denticity|octadentate]] N₂O₆ ligand. The resulting cation K([2.2.2]cryptand)⁺ is lipophilic.

[[Image:Cryptate of potassium cation.jpg|thumbnail|left|Structure of [2.2.2]cryptand encapsulating a [[potassium]] cation (purple) as determined by [[X-ray crystallography]]<ref>{{cite journal |author1=Alberto, R. |author2=Ortner, K. |author3=Wheatley, N. |author4=Schibli, R. |author5=Schubiger, A. P. | title = Synthesis and properties of boranocarbonate: a convenient in situ CO source for the aqueous preparation of [^99mTc(OH₂)₃(CO)₃]⁺ | journal = [[J. Am. Chem. Soc.]] | year = 2001 | volume = 121 | pages = 3135–3136 | doi = 10.1021/ja003932b |pmid=11457025 | issue = 13}}</ref>]]{{clear-left}}

==References==

{{Reflist}}

{{DEFAULTSORT:Cryptand, 2.2.2-}}

[[Category:Chelating agents]]