Carbanion mechanisms XXI. Solution acidity of triphenylsilane

Comparative acidity measurements have been performed between triphenylsilylpotassium and a series of arylmethanes by 1H-NMR in tetrahydrofuran: Ph 3 SiK+ Ar n CH 4 −n ⇆Ph 3 SiH+ Ar n CH 3 −n K Metalation of the arylmethane was complete in the case of Ph 3CH (p K a 31.4) and Ph 2CH 2 (p K a 33.4) but...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 604; no. 2; pp. 208 - 210
Main Authors Buncel, Erwin, Venkatachalam, T.K.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 16.06.2000
Subjects
Acidity
p Ka in THF
Silyl anions
Triphenylsilane
Triphenylsilane
Silyl anions
Acidity
p K a in THF
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Summary:Comparative acidity measurements have been performed between triphenylsilylpotassium and a series of arylmethanes by 1H-NMR in tetrahydrofuran: Ph 3 SiK+ Ar n CH 4 −n ⇆Ph 3 SiH+ Ar n CH 3 −n K Metalation of the arylmethane was complete in the case of Ph 3CH (p K a 31.4) and Ph 2CH 2 (p K a 33.4) but with ( p-CH 3·C 6H 4) 2CH 2 (p K a 35.1) ∼50% metalation of the di- p-tolymethane occurred, indicating that the two acids have equal p K a. No reaction occurred with 4-Ph·C 6H 4·CH 3 (p K a 38.7). Thus p K a Ph 3SiH≈35.1 in THF. This represents the first solution measurement of the acidity of an organosilane.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(00)00242-4