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IUPAC name
3D model (JSmol)
Molar mass 139.22 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Oxatriquinane is an alkyl oxonium ion with formula C
, remarkable for being stable in aqueous solution. It has a cyclononane backbone, with the trivalent oxygen connected to carbons 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]


Related 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]


  1. ^ a b c d Mark Mascal; Nema Hafezi; Nabin K. Meher & James C. Fettinger (2008). "Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions". Journal of the American Chemical Society. 130 (41): 13532–13533. doi:10.1021/ja805686u. PMID 18798616. 
  2. ^ Rachel Petkewich (September 29, 2008). "Taming Alkyl Oxonium Ions: Fused tricyclic structure stabilizes famously reactive alkylating agents". Chemical and Engineering News. 86 (39): 10. doi:10.1021/cen-v086n039.p010. 
  3. ^ Tim Reid (3 October 2008). "Oxonium ions: Ring of stability". Nature Chemistry. doi:10.1038/nchem.70. 
  4. ^ Stoyanov, Evgenii S.; Gunbas, Gorkem; Hafezi, Nema; Mascal, Mark; Stoyanova, Irini V.; Tham, Fook S.; Reed, Christopher A. (11 January 2012). "The R3O+···H+ Hydrogen Bond: Toward a Tetracoordinate Oxadionium(2+) Ion". Journal of the American Chemical Society. 134 (1): 707–714. doi:10.1021/ja209942s. 
  5. ^ Gunbas, Gorkem; Hafezi, Nema; Sheppard, William L.; Olmstead, Marilyn M.; Stoyanova, Irini V.; Tham, Fook S.; Meyer, Matthew P.; Mascal, Mark (18 November 2012). "Extreme oxatriquinanes and a record C–O bond length". Nature Chemistry. 4 (12): 1018–1023. Bibcode:2012NatCh...4.1018G. doi:10.1038/nchem.1502.