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- Arenium_ion abstract "An arenium ion in organic chemistry is a cyclohexadienyl cation that appears as a reactive intermediate in electrophilic aromatic substitution. For historic reasons this complex is also called a Wheland intermediate or a sigma complex or σ-complex. The smallest arenium ion is benzenium ion C6H7+, which is protonated benzene. benzenium ionTwo hydrogen atoms bonded to one carbon lie in a plane perpendicular to the benzene ring. The arenium ion is no longer an aromatic species; however it is relatively stable due to delocalization: the positive charge is delocalized over 3 carbon atoms via the pi system, as depicted on the following resonance structures: Arenium Ion Resonance structuresA complexed electrophile can contribute to the stability of arenium ions. A benzenium ion can be isolated as a stable compound when benzene is protonated by the carborane superacid H(CB11H(CH3)5Br6). The benzenium salt is crystalline with thermal stability up to 150 °C. Bond lengths deduced from X-ray crystallography are consistent with a cyclohexadienyl cation structure.In one study a methylene arenium ion is stabilized by metal complexation:Methylene arenium ionIn this reaction sequence the R-Pd(II)-Br starting complex 1 stabilized by TMEDA is converted by dppe to metal complex 2. Electrophilic attack of methyl triflate forms methylene arenium ion 3 with (based on X-ray crystallography) positive charge located in aromatic para position and with the methylene group 6° out of the plane of the ring. Reaction first with water and then with triethylamine hydrolyzes the ether group.".
- Arenium_ion thumbnail Benzenium-3D-balls.png?width=300.
- Arenium_ion wikiPageID "3461886".
- Arenium_ion wikiPageLength "3652".
- Arenium_ion wikiPageOutDegree "28".
- Arenium_ion wikiPageRevisionID "639147213".
- Arenium_ion wikiPageWikiLink 1,2-Bis(diphenylphosphino)ethane.
- Arenium_ion wikiPageWikiLink Arene_substitution_pattern.
- Arenium_ion wikiPageWikiLink Aryl_radical.
- Arenium_ion wikiPageWikiLink Benzene.
- Arenium_ion wikiPageWikiLink Bond_length.
- Arenium_ion wikiPageWikiLink Carborane_acid.
- Arenium_ion wikiPageWikiLink Category:Carbocations.
- Arenium_ion wikiPageWikiLink Category:Cations.
- Arenium_ion wikiPageWikiLink Category:Reactive_intermediates.
- Arenium_ion wikiPageWikiLink Dewar–Chatt–Duncanson_model.
- Arenium_ion wikiPageWikiLink Electrophile.
- Arenium_ion wikiPageWikiLink Electrophilic_aromatic_substitution.
- Arenium_ion wikiPageWikiLink Ether.
- Arenium_ion wikiPageWikiLink Ion.
- Arenium_ion wikiPageWikiLink List_of_important_publications_in_chemistry.
- Arenium_ion wikiPageWikiLink Methyl_trifluoromethansulfonate.
- Arenium_ion wikiPageWikiLink Methylene_group.
- Arenium_ion wikiPageWikiLink Organic_chemistry.
- Arenium_ion wikiPageWikiLink Pi_bond.
- Arenium_ion wikiPageWikiLink Resonance_(chemistry).
- Arenium_ion wikiPageWikiLink Tetramethylethylenediamine.
- Arenium_ion wikiPageWikiLink Triethylamine.
- Arenium_ion wikiPageWikiLink X-ray_crystallography.
- Arenium_ion wikiPageWikiLink File:AreniumIon.png.
- Arenium_ion wikiPageWikiLink File:AreniumIonResonance.png.
- Arenium_ion wikiPageWikiLink File:Benzenium-3D-balls.png.
- Arenium_ion wikiPageWikiLink File:Methyleneareniumion.png.
- Arenium_ion wikiPageWikiLinkText "Arenium ion".
- Arenium_ion wikiPageWikiLinkText "arenium ion".
- Arenium_ion wikiPageWikiLinkText "benzenium".
- Arenium_ion wikiPageWikiLinkText "protonated benzene".
- Arenium_ion wikiPageUsesTemplate Template:Reflist.
- Arenium_ion subject Category:Carbocations.
- Arenium_ion subject Category:Cations.
- Arenium_ion subject Category:Reactive_intermediates.
- Arenium_ion hypernym Cation.
- Arenium_ion type ChemicalCompound.
- Arenium_ion type Cation.
- Arenium_ion comment "An arenium ion in organic chemistry is a cyclohexadienyl cation that appears as a reactive intermediate in electrophilic aromatic substitution. For historic reasons this complex is also called a Wheland intermediate or a sigma complex or σ-complex. The smallest arenium ion is benzenium ion C6H7+, which is protonated benzene. benzenium ionTwo hydrogen atoms bonded to one carbon lie in a plane perpendicular to the benzene ring.".
- Arenium_ion label "Arenium ion".
- Arenium_ion sameAs Q642076.
- Arenium_ion sameAs Areniumion.
- Arenium_ion sameAs Catión_arenio.
- Arenium_ion sameAs Ione_arenio.
- Arenium_ion sameAs アレニウムイオン.
- Arenium_ion sameAs Areniumion.
- Arenium_ion sameAs m.09drh8.
- Arenium_ion sameAs Q642076.
- Arenium_ion wasDerivedFrom Arenium_ion?oldid=639147213.
- Arenium_ion depiction Benzenium-3D-balls.png.
- Arenium_ion isPrimaryTopicOf Arenium_ion.