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- Oxonium_ion abstract "In chemistry, an oxonium ion is any oxygen cation with three bonds. The simplest oxonium ion is the hydronium ion H3O+. Another class of oxonium ions frequently encountered in organic chemistry is the oxocarbenium ions, obtained by protonation or alkylation of a carbonyl group e.g. R-C=O+-R' which forms a resonance structure with the fully fledged carbocation R-C+-O-R' and is therefore especially stable:250pxStable alkyloxonium salts exist; they are extensively used as alkylating agents. For example, triethyloxonium tetrafluoroborate (Et3O+)(BF−4) is a white crystalline solid. It is a powerful ethylating agent. It can be used, for example, to produce ethyl esters when the conditions of traditional Fischer esterification are unsuitable.Other hydrocarbon oxonium ions are formed by protonation or alkylation of alcohols or ethers (R-C-O+-R1R2). In acidic media, the oxonium functional group produced by protonating an alcohol can be a leaving group in the E2 elimination reaction, because when it receives an electron, it becomes a water molecule. The product is an alkene. Extreme acidity, heat and dehydrating conditions are usually required.Oxatriquinane and oxatriquinacene are unusually stable oxonium ions, first described in 2008. Oxatriquinane 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.".
- Oxonium_ion thumbnail Carbonyl-oxonium-resonance-2D-skeletal.png?width=300.
- Oxonium_ion wikiPageID "521970".
- Oxonium_ion wikiPageLength "2562".
- Oxonium_ion wikiPageOutDegree "44".
- Oxonium_ion wikiPageRevisionID "611588438".
- Oxonium_ion wikiPageWikiLink Alcohol.
- Oxonium_ion wikiPageWikiLink Alkene.
- Oxonium_ion wikiPageWikiLink Alkyl.
- Oxonium_ion wikiPageWikiLink Alkylation.
- Oxonium_ion wikiPageWikiLink Amine.
- Oxonium_ion wikiPageWikiLink Azide.
- Oxonium_ion wikiPageWikiLink Ball-and-stick_model.
- Oxonium_ion wikiPageWikiLink Carbocation.
- Oxonium_ion wikiPageWikiLink Carbonyl.
- Oxonium_ion wikiPageWikiLink Category:Oxycations.
- Oxonium_ion wikiPageWikiLink Cation.
- Oxonium_ion wikiPageWikiLink Chemical_bond.
- Oxonium_ion wikiPageWikiLink Chemistry.
- Oxonium_ion wikiPageWikiLink Cyanide.
- Oxonium_ion wikiPageWikiLink Elimination_reaction.
- Oxonium_ion wikiPageWikiLink Ester.
- Oxonium_ion wikiPageWikiLink Esterification.
- Oxonium_ion wikiPageWikiLink Functional_group.
- Oxonium_ion wikiPageWikiLink Halide.
- Oxonium_ion wikiPageWikiLink Halide_ion.
- Oxonium_ion wikiPageWikiLink Hydronium.
- Oxonium_ion wikiPageWikiLink Hydroxide.
- Oxonium_ion wikiPageWikiLink Ion.
- Oxonium_ion wikiPageWikiLink Leaving_group.
- Oxonium_ion wikiPageWikiLink Nucleophile.
- Oxonium_ion wikiPageWikiLink Onium_compound.
- Oxonium_ion wikiPageWikiLink Onium_compounds.
- Oxonium_ion wikiPageWikiLink Organic_chemistry.
- Oxonium_ion wikiPageWikiLink Oxatriquinacene.
- Oxonium_ion wikiPageWikiLink Oxatriquinane.
- Oxonium_ion wikiPageWikiLink Oxocarbenium.
- Oxonium_ion wikiPageWikiLink Oxygen.
- Oxonium_ion wikiPageWikiLink Protonation.
- Oxonium_ion wikiPageWikiLink Pyrylium_salt.
- Oxonium_ion wikiPageWikiLink Resonance_(chemistry).
- Oxonium_ion wikiPageWikiLink Resonance_structure.
- Oxonium_ion wikiPageWikiLink Salt_(chemistry).
- Oxonium_ion wikiPageWikiLink Salts.
- Oxonium_ion wikiPageWikiLink Skeletal_formula.
- Oxonium_ion wikiPageWikiLink Space-filling_model.
- Oxonium_ion wikiPageWikiLink Thiol.
- Oxonium_ion wikiPageWikiLink Triethyloxonium_tetrafluoroborate.
- Oxonium_ion wikiPageWikiLink Trigonal_pyramidal_molecular_geometry.
- Oxonium_ion wikiPageWikiLink Water.
- Oxonium_ion wikiPageWikiLink File:Carbonyl-oxonium-resonance-2D-skeletal.png.
- Oxonium_ion wikiPageWikiLink File:Oxonium-ion-2D.png.
- Oxonium_ion wikiPageWikiLink File:Trimethyloxonium-2D-skeletal.png.
- Oxonium_ion wikiPageWikiLink File:Trimethyloxonium-3D-balls.png.
- Oxonium_ion wikiPageWikiLink File:Trimethyloxonium-3D-vdW.png.
- Oxonium_ion wikiPageWikiLinkText "Oxonium ion".
- Oxonium_ion wikiPageWikiLinkText "oxonium ion".
- Oxonium_ion wikiPageWikiLinkText "oxonium salt".
- Oxonium_ion wikiPageWikiLinkText "oxonium".
- Oxonium_ion wikiPageWikiLinkText "trialkyloxonium salts".
- Oxonium_ion hasPhotoCollection Oxonium_ion.
- Oxonium_ion wikiPageUsesTemplate Template:Chem.
- Oxonium_ion wikiPageUsesTemplate Template:Morefootnotes.
- Oxonium_ion wikiPageUsesTemplate Template:Reflist.
- Oxonium_ion subject Category:Oxycations.
- Oxonium_ion type Article.
- Oxonium_ion type Article.
- Oxonium_ion type Cation.
- Oxonium_ion comment "In chemistry, an oxonium ion is any oxygen cation with three bonds. The simplest oxonium ion is the hydronium ion H3O+. Another class of oxonium ions frequently encountered in organic chemistry is the oxocarbenium ions, obtained by protonation or alkylation of a carbonyl group e.g. R-C=O+-R' which forms a resonance structure with the fully fledged carbocation R-C+-O-R' and is therefore especially stable:250pxStable alkyloxonium salts exist; they are extensively used as alkylating agents.".
- Oxonium_ion label "Oxonium ion".
- Oxonium_ion sameAs أيون_أوكسونيوم.
- Oxonium_ion sameAs Oxoniový_ion.
- Oxonium_ion sameAs Oxonium.
- Oxonium_ion sameAs یون_اکسونیوم.
- Oxonium_ion sameAs Oksoniumioni.
- Oxonium_ion sameAs Ion_oxonium.
- Oxonium_ion sameAs オキソニウムイオン.
- Oxonium_ion sameAs Oxonium.
- Oxonium_ion sameAs Oksoniumion.
- Oxonium_ion sameAs Jon_oksoniowy.
- Oxonium_ion sameAs Íon_oxônio.
- Oxonium_ion sameAs m.02l4ln.
- Oxonium_ion sameAs Q132187.
- Oxonium_ion sameAs Q132187.
- Oxonium_ion sameAs 𨦡鹽.
- Oxonium_ion wasDerivedFrom Oxonium_ion?oldid=611588438.
- Oxonium_ion depiction Carbonyl-oxonium-resonance-2D-skeletal.png.
- Oxonium_ion isPrimaryTopicOf Oxonium_ion.