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Revision as of 16:49, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 466616366 of page 15-Crown-5 for the Chem/Drugbox validation project (updated: 'ChEBI').  Latest revision as of 22:00, 26 April 2024 edit Arun 01 (talk | contribs)Extended confirmed users1,143 editsm Improved wordingTag: Visual edit 
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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.}}
{{Chembox {{Chembox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 457644056 | verifiedrevid = 477209069
| ImageFile = 15-crown-5 skeletal.svg | ImageFile = 15-crown-5 skeletal.svg
| ImageSize = 150 | ImageSize = 150
Line 10: Line 9:
| ImageSize1 = 170 | ImageSize1 = 170
| ImageAlt1 = Ball-and-stick model | ImageAlt1 = Ball-and-stick model
| SystematicName = 1,4,7,10,13-Pentaoxacyclopentadecane<ref>{{Cite web|title = 15-crown-5 - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=36336&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 11 October 2011|location = USA|date = 16 September 2004|at = Identification and Related Records}}</ref> | PIN = 1,4,7,10,13-Pentaoxacyclopentadecane<ref>{{Cite web|title = 15-crown-5 - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=36336&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 11 October 2011|location = USA|date = 16 September 2004|at = Identification and Related Records}}</ref>
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 33100-27-5 | CASNo = 33100-27-5
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 36336 | PubChem = 36336
| ChemSpiderID = 33416
| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 33416
| EINECS = 251-379-6
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 251-379-6 | MeSHName = 15-Crown-5
| MeSHName = 15-Crown-5 | ChEBI = 32401
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 32401
| ChEMBL = 156289
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 156289
| RTECS = SB0200000
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = SB0200000 | Beilstein = 1618144
| Beilstein = 1618144 | Gmelin = 3897
| SMILES = C1COCCOCCOCCOCCO1
| Gmelin = 3897
| StdInChI = 1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
| SMILES = C1COCCOCCOCCOCCO1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
| InChI = 1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VFTFKUDGYRBSAL-UHFFFAOYSA-N
| InChI = 1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VFTFKUDGYRBSAL-UHFFFAOYSA-N
| InChIKey = VFTFKUDGYRBSAL-UHFFFAOYAH
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = VFTFKUDGYRBSAL-UHFFFAOYAH
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 10 | C=10 | H=20 | O=5
| Appearance = Clear, colorless liquid
| H = 20
| Density = 1.113 g cm<sup>−3</sup> (at 20 °C)
| O = 5
| BoilingPtC = 93-96
| ExactMass = 220.131073750 g mol<sup>-1</sup>
| BoilingPt_notes = at 0.05 mmHg
| Appearance = Transparent liquid
| LogP = -0.639
| Density = 1.113 g cm<sup>-3</sup> (at 20 °C)
| BoilingPtC = 116 | RefractIndex = 1.465
| Boiling_notes = at 240 Pa
| LogP = -0.639
| RefractIndex = 1.465
}} }}
| Section3 = {{Chembox Thermochemistry |Section3={{Chembox Thermochemistry
| DeltaHf = -881.1--877.1 kJ mol<sup>-1</sup> | DeltaHf = -881.1--877.1 kJ mol<sup>−1</sup>
| DeltaHc = -5.9157--5.9129 MJ mol<sup>-1</sup> | DeltaHc = -5.9157--5.9129 MJ mol<sup>−1</sup>
}} }}
| Section4 = {{Chembox Hazards |Section4={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| GHSPictograms = {{GHS exclamation mark}} | GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING''' | GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|302|315|319}} | HPhrases = {{H-phrases|302|315|319}}
| PPhrases = {{P-phrases|305+351+338}} | PPhrases = {{P-phrases|305+351+338}}
| NFPA-F = 1
| EUClass = {{Hazchem Xn}}
| NFPA-H = 2
| RPhrases = {{R22}}, {{R36/38}}
| SPhrases = {{S26}} | NFPA-R = 0
| NFPA-F = 1 | FlashPtC = 113
| NFPA-H = 2
| NFPA-R = 0
| FlashPt = 113 °C
}} }}
}} }}

'''15-Crown-5''' is a ] with the formula (C<sub>2</sub>H<sub>4</sub>O)<sub>5</sub>. It is a cyclic pentamer of ] that forms complex with various ]s, including ] (Na<sup>+</sup>)<ref>
{{cite journal
| url=https://www.jstage.jst.go.jp/browse/bcsj/61/3/_contents
| author=Takeda, Y. | title = A Conductance Study of 1:1 Complexes of 15-Crown-5, 16-Crown-5, and Benzo-15-crown-5 with Alkali Metal Ions in Nonaqueous Solvents | journal = Bulletin of the Chemical Society of Japan | year = 1988 | volume = 61 | issue = 3 | pages = 627–632 | doi=10.1246/bcsj.61.627|display-authors=etal| doi-access = free }}
</ref> and ] (K<sup>+</sup>);<ref>
{{cite journal
| url=http://www.rsc.org/publishing/journals/CC/article.asp?doi=b512677k
| author=Chen, Chun-Yen | title = Potassium ion recognition by 15-crown-5 functionalized CdSe/ZnS quantum dots in H<sub>2</sub>O | journal = Chem. Comm. | year = 2006 | pages = 263–265
| doi=10.1039/B512677K
| issue=3| pmid=16391728 |display-authors=etal}}</ref> however, it is complementary to Na<sup>+</sup> and thus has a higher selectivity for Na<sup>+</sup> ions.

== Synthesis ==
15-Crown-5 can be synthesized using a modified ]:<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>

:(CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>Cl)<sub>2</sub> + O(CH<sub>2</sub>CH<sub>2</sub>OH)<sub>2</sub> + 2 NaOH → (CH<sub>2</sub>CH<sub>2</sub>O)<sub>5</sub> + 2 NaCl + 2 H<sub>2</sub>O

It also forms from the cyclic ] of ethylene oxide in the presence of gaseous ].<ref>{{Citation|last1=Liotta|first1=Charles L.|title=15-Crown-5|date=2001|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|place=Chichester, UK|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/047084289x.rc263|isbn=978-0-471-93623-7|last2=Berkner|first2=Joachim}}</ref>

==Properties==
Analogous to ], 15-crown-5 binds to sodium ions. Thus, when treated with this complexing agent, sodium salts often become soluble in organic solvents.

First-row transition metal dications fit snugly inside the cavity of 15-crown-5. They are too small to be included in 18-crown-6. The binding of transition metal cations results in multiple hydrogen-bonded interactions from both equatorial and axial aqua ligands, such that highly crystalline solid-state supramolecular polymers can be isolated. Metal salts isolated in this form include Co(ClO<sub>4</sub>)<sub>2</sub>, Ni(ClO<sub>4</sub>)<sub>2</sub>, Cu(ClO<sub>4</sub>)<sub>2</sub>, and Zn(ClO<sub>4</sub>)<sub>2</sub>. Seven coordinate species are most common for transition metal complexes of 15-crown-5, with the crown ether occupying the equatorial plane, along with 2 axial aqua ligands.<ref name="SupraChem">{{cite book
| title = Supramolecular Chemistry, 2nd edition
| chapter =
| author1 = Jonathan W. Steed
| author2 = Jerry L. Atwood
| publisher = Wiley
| year = 2009
| isbn = 978-0-470-51233-3
| page =
}}</ref>

<sup>2+</sup>}}.]]

15-crown-5 has also been used to isolate salts of oxonium ions. For example, from a solution of ], the oxonium ion {{nowrap|<sup>+</sup>}} has been isolated as the salt {{nowrap|}}. ] studies revealed a sandwich structure, which shows a chain of water with remarkably long O-H bond (1.12 Å) in the acidic proton, but with a very short OH•••O distance (1.32 Å).<ref name="SupraChem" />

<sup>+</sup>}} ion]]

A derivative of 15-crown-5, benzo-15-crown-5, has been used to produce anionic complexes of carbido ]s as their {{nowrap|<sup>+</sup>}} salts:<ref name="SupraChem" />
:{{nowrap|(Ar<sub>2</sub>N)<sub>3</sub>MoCH + KCH<sub>2</sub>Ph + 2 (15-crown-5) → <sup>+</sup><sup>−</sup> + CH<sub>3</sub>Ph}}

==See also==
* ]
* ]

==References==
{{Reflist}}

==Further reading==
*{{cite journal
| url=http://infoscience.epfl.ch/record/52153
| author=Klok, H.A. | title = Novel benzo-15-crown-5 functionalized α-olefin/CO terpolymers for membrane applications | journal = Macromolecular Chemistry and Physics | year = 1997 | volume = 198 | issue = 9 | pages = 2759–2768
| doi=10.1002/macp.1997.021980908|display-authors=etal}}
*{{cite journal
| url=http://www.arkat-usa.org/get-file/19080/
| author=Fedorova, O.A. | title = Facile synthesis of novel styryl ligands containing a 15-crown-5 ether moiety | journal = Arkivoc | year = 2005 | volume = xv | pages = 12–24| doi=10.3998/ark.5550190.0006.f03 |display-authors=etal| doi-access = free | hdl = 2027/spo.5550190.0006.f03 | hdl-access = free }}

==External links==
*
*

{{DEFAULTSORT:Crown-5, 15-}}
]
Misplaced Pages:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 15-Crown-5: Difference between pages Add topic