| 词条 | Oxatriquinane | ||
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 429969980 | ImageFileL1 = Oxatriquinane.svg | ImageAltL1 = | ImageFileR1 = Oxatriquinane.png | ImageAltR1 = | IUPACName = (2as,4as,6as)-Octahydro-1H-2a1-oxacyclopenta[cd]pentalen-2a1-ium | OtherNames = |Section1={{Chembox Identifiers | CASNo = 1056549-35-9 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = | SMILES = [H][C@@]12[O+]3[C@@](CC2)([H])CC[C@]3([H])CC1 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 21402960 | InChI = 1/C9H15O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h7-9H,1-6H2/q+1/t7-,8+,9- | InChIKey = BVKXDOLLNZJDKZ-AYMMMOKOBR | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C9H15O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h7-9H,1-6H2/q+1/t7-,8+,9- | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = BVKXDOLLNZJDKZ-AYMMMOKOSA-N}} |Section2={{Chembox Properties | C=9 | H=15 | O=1 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Oxatriquinane is an alkyl oxonium ion with formula {{chem|C|9|H|15|O|+}}, remarkable for being stable in aqueous solution. It has a cyclononane backbone, with a trivalent oxygen connected to carbon 1, 4, and 7, forming three fused pentagonal rings. Oxatriquinane was first described in 2008, and was obtained after a five-step synthesis starting from 1,4,7-cyclononatriene.[1][2][3] At the time it had the longest C–O bond lengths (1.54 Å, C–O bonds in ethers are generally ~1.43 Å) and most acute C−O−C angles ever observed in a compound.[1] Oxonium ions normally are strong alkylating agents and are only observed in solution as reactive intermediates or under extreme conditions. Oxatriquinane is an exception: it does not react with boiling water or with alcohols, thiols, halide ions, or amines, although it does react with stronger nucleophiles such as hydroxide, cyanide, and azide.[1] The ability of the oxygen to enter into a fourth covalent bond has been of some theoretical interest and was achieved using carborane acid.[4] AnaloguesRelated species include oxatriquinacene,[1] the tri-unsaturated analogue, which is of interest as a possible precursor to oxaacepentalene, a neutral aromatic species. 1,4,7-tri-tert-butyloxatriquinane has also been synthesised; this compound contains significant amounts of intramolecular steric strain, resulting in further bond elongation to give C–O bond lengths of 1.622 Å, the longest recorded in any species.[5] References1. ^1 2 3 {{cite journal |title=Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions |author1=Mark Mascal |author2=Nema Hafezi |author3=Nabin K. Meher |author4=James C. Fettinger |last-author-amp=yes |pages=13532–13533 |doi=10.1021/ja805686u |volume=130 |year=2008 |journal=Journal of the American Chemical Society |pmid=18798616 |issue=41}} 2. ^ {{cite journal |date=September 29, 2008 |volume=86 |issue=39 |pages=10 |title=Taming Alkyl Oxonium Ions: Fused tricyclic structure stabilizes famously reactive alkylating agents |author=Rachel Petkewich |journal=Chemical and Engineering News |url=http://pubs.acs.org/cen/news/86/i39/8639notw6.html |doi=10.1021/cen-v086n039.p010}} 3. ^ {{cite journal |journal=Nature Chemistry |title=Oxonium ions: Ring of stability |author=Tim Reid |doi=10.1038/nchem.70 |date=3 October 2008}} 4. ^{{cite journal|last1=Stoyanov|first1=Evgenii S.|last2=Gunbas|first2=Gorkem|last3=Hafezi|first3=Nema|last4=Mascal|first4=Mark|last5=Stoyanova|first5=Irini V.|last6=Tham|first6=Fook S.|last7=Reed|first7=Christopher A.|title=The R3O+···H+ Hydrogen Bond: Toward a Tetracoordinate Oxadionium(2+) Ion|journal=Journal of the American Chemical Society|date=11 January 2012|volume=134|issue=1|pages=707–714|doi=10.1021/ja209942s|pmid=22133059|pmc=3257418}} 5. ^{{cite journal|last1=Gunbas|first1=Gorkem|last2=Hafezi|first2=Nema|last3=Sheppard|first3=William L.|last4=Olmstead|first4=Marilyn M.|last5=Stoyanova|first5=Irini V.|last6=Tham|first6=Fook S.|last7=Meyer|first7=Matthew P.|last8=Mascal|first8=Mark|title=Extreme oxatriquinanes and a record C–O bond length|journal=Nature Chemistry|date=18 November 2012|volume=4|issue=12|pages=1018–1023|doi=10.1038/nchem.1502|pmid=23174982|bibcode=2012NatCh...4.1018G}} 2 : Oxycations|Oxygen heterocycles |
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