| Revision as of 16:47, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443261170 of page 12-Crown-4 for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 10:55, 1 June 2023 edit Graeme Bartlett (talk | contribs)Administrators249,763 edits added Category:Twelve-membered rings using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443259844 |
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| verifiedrevid = 477208843 |
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| ImageFile = 12-crown-4 skeletal.svg |
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| ImageFileL1 = 12-crown-4 skeletal.svg |
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| ImageSize = |
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| ImageSizeL1 = 125 |
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| IUPACName = 1,4,7,10-tetraoxacyclododecane |
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| ImageAltL1 = Skeletal formula of 12-crown-4 |
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| ImageFileR1 = 12-Crown-4-3D-balls.png |
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| ImageSizeR1 = 135 |
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| ImageAltR1 = Ball-and-stick model of the 12-Crown-4 molecule |
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| PIN = 1,4,7,10-Tetraoxacyclododecane |
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| OtherNames = 12-crown-4, Lithium Ionophore V |
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| OtherNames = 12-crown-4, Lithium Ionophore V |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChEBI = 32399 |
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| ChEBI = 32399 |
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| ChemSpiderID = 8912 |
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| ChemSpiderID = 8912 |
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| PubChem = 9269 |
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| EC_number = 206-036-5 |
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| UNII = K6069P2C2A |
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| Beilstein = 1363064 |
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| Gmelin = 3287 |
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| InChI = 1/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2 |
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| InChI = 1/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2 |
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| InChIKey = XQQZRZQVBFHBHL-UHFFFAOYAA |
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| InChIKey = XQQZRZQVBFHBHL-UHFFFAOYAA |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 294-93-9 |
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| CASNo = 294-93-9 |
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| SMILES = O1CCOCCOCCOCC1 |
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| PubChem = |
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| SMILES = O1CCOCCOCCOCC1 |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| MolarMass = 176.21 |
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| MolarMass = 176.21 |
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| Appearance = |
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| Appearance = |
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| Density = 1.089 g/mL at 25 deg C |
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| Density = 1.089 g/mL at 25 °C |
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| MeltingPt = 16 deg C |
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| MeltingPt = 16 °C |
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| BoilingPt = 61-70 deg C/0.5 mm Hg |
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| BoilingPt = 61-70 °C/0.5 mm Hg |
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| Solubility = |
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| Solubility = Miscible |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = 113 deg C |
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| FlashPtC = 113 |
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| Autoignition = |
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| AutoignitionPtC = |
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| HPhrases = {{H-phrases}} |
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| PPhrases = {{P-phrases}} --> |
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'''12-Crown-4''', also called 1,4,7,10-tetraoxacyclododecane and lithium ] V, is a ] with the formula C<sub>8</sub>H<sub>16</sub>O<sub>4</sub>. It is a cyclic ] of ] which is specific for the lithium cation. |
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== Synthesis == |
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12-Crown-4 can be synthesized using a modified ], using ] as a templating cation:<ref>{{Cite journal|last1=Cook|first1=Fred L.|last2=Caruso|first2=Thomas C.|last3=Byrne|first3=Michael P.|last4=Bowers|first4=Chauncey W.|last5=Speck|first5=Don H.|last6=Liotta|first6=Charles L.|date=1974|title=Facile syntheses of 12-crown-4 and 15-crown-5|journal=Tetrahedron Letters|language=en|volume=15|issue=46|pages=4029–4032|doi=10.1016/S0040-4039(01)92075-1}}</ref> |
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: (CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>Cl)<sub>2</sub> + (CH<sub>2</sub>OH)<sub>2</sub> + 2 NaOH → (CH<sub>2</sub>CH<sub>2</sub>O)<sub>4</sub> + 2 NaCl + 2 H<sub>2</sub>O |
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It also forms from the cyclic ] of ethylene oxide in the presence of gaseous ].<ref name="e-EROS">{{Citation|last1=Liotta|first1=Charles L.|title=12-Crown-4|date=2001|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|place=Chichester, UK|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/047084289X.rc262|isbn=978-0-471-93623-7|last2=Berkner|first2=Joachim}}</ref> |
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== Properties == |
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] |
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Like other crown ethers, 12-crown-4 complexes with alkali metal cations. The cavity diameter of 1.2-1.5 Å gives it a high selectivity towards the lithium cation (ionic diameter 1.36 Å)<ref name="e-EROS"/> |
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Its ] is S<sub>4</sub>. The dipole moment of 12-crown-4 varies with solvent and temperature. At 25 °C, the dipole moment of 12-crown-4 was determined as 2.33 ± 0.03 D in cyclohexane and 2.46 ± 0.01 D in benzene.<ref>{{cite journal|last1=Caswell|first1=Lyman R.|last2=Savannunt|first2=Diana S.|title=Temperature and solvent effects on the experimental dipole moments of three crown ethers|journal=Journal of Heterocyclic Chemistry|date=January 1988|volume=25|issue=1|pages=73–79|doi=10.1002/jhet.5570250111}}</ref> |
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==References== |
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{{Reflist}} |
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* ] Handbook of Fine Chemicals, 2007, page 768. |
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* ] Cyclic tetramer of ethylene oxide which is specific for the lithium cation. 98%, 2018 |
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==See also== |
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*] |
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*], a similar molecule with N atoms (aza groups) instead of O atoms (ethers) |
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{{DEFAULTSORT:Crown-4, 12-}} |
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] |
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] |