| dbo:abstract |
A silylium ion is a reactive silyl-containing cation with the formula SiR+3. With three rather than the usual four bonds to Si, silylium ions are the silicon analogues of carbenium ions. They can be viewed as protonated silylenes. Early efforts to generate these cations produced salts of the pyridine complex [(CH3)3Si-NC5H5]+, the hydride-bridged species [(Et3Si)2H]+, and the toluene complex [(mes)3Si(toluene)]+. Well-characterized silylium salts with well-defined three-coordinate silicon cations trimesitylsilylium Si(C6H2Me3)+3 and tris(pentamethylphenyl) Si(C6Me5)+3. These cations are related to trityl (C(C6H5)+3), with the extra methyl groups providing steric protection, compensating for the greater size of Si vs C. Its 29Si NMR chemical shift is 225.5 ppm, downfield of TMS, which indicates that the cation is quite "naked". Trimethylsilyl trifluoromethanesulfonate (Me3SiOTf), normally considered a source of electrophilic silicon, has a 29Si NMR shift of 43 ppm. Salts of Si(C6H2Me3)+3 and Si(C6Me5)+3 have been crystallized with the carborane [HCB11Me5Br6]− and decaborate [B12Cl12]2-, respectively. Weakly coordinating anions are essential for the isolation of these highly electrophilic cations. (en) |
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wiki-commons:Special:FilePath/SiMes3+.png?width=300 |
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| dbo:wikiPageWikiLink |
dbr:Carbenium_ion dbc:Cations dbr:Organosilicon_compound dbr:Silylene dbr:Trimethylsilyl_trifluoromethanesulfonate dbc:Silicon dbr:Carborane dbc:Reactive_intermediates dbr:Methyl dbr:Weakly_coordinating_anion dbr:Trityl dbr:File:SiMes3+.png |
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dbt:Chem dbt:Chem-stub |
| dcterms:subject |
dbc:Cations dbc:Silicon dbc:Reactive_intermediates |
| gold:hypernym |
dbr:Cation |
| rdf:type |
yago:Abstraction100002137 yago:Chemical114806838 yago:Intermediate114921272 yago:Material114580897 yago:Matter100020827 yago:Part113809207 yago:PhysicalEntity100001930 yago:Relation100031921 dbo:ChemicalCompound yago:Substance100019613 yago:WikicatReactiveIntermediates |
| rdfs:comment |
A silylium ion is a reactive silyl-containing cation with the formula SiR+3. With three rather than the usual four bonds to Si, silylium ions are the silicon analogues of carbenium ions. They can be viewed as protonated silylenes. Early efforts to generate these cations produced salts of the pyridine complex [(CH3)3Si-NC5H5]+, the hydride-bridged species [(Et3Si)2H]+, and the toluene complex [(mes)3Si(toluene)]+. (en) |
| rdfs:label |
Silylium ion (en) |
| owl:sameAs |
freebase:Silylium ion yago-res:Silylium ion wikidata:Silylium ion https://global.dbpedia.org/id/enD8 |
| prov:wasDerivedFrom |
wikipedia-en:Silylium_ion?oldid=1012737656&ns=0 |
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wiki-commons:Special:FilePath/SiMes3+.png |
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wikipedia-en:Silylium_ion |
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dbr:Silylium |
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dbr:Nucleophilic_abstraction dbr:M-Terphenyl dbr:Silylene dbr:Onium_ion dbr:Silylium |
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wikipedia-en:Silylium_ion |
