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Determination of the Solution Acidity of Tris(trimethylsilyl)silane

Summary: Determination of the Solution Acidity of
Gady Korogodsky, Michael Bendikov, Dmitry Bravo-Zhivotovskii, and
Yitzhak Apeloig*
Department of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum
Chemistry, Technion-Israel Institute of Technology, Haifa 32000, Israel
Received September 11, 2001
The acidity of (Me3Si)3SiH was determined in diethyl ether solution by reactions of (Me3-
Si)3SiLi,3THF with a series of C-H acids. (Me3Si)3SiH and 9-phenylxanthyllithium (pK )
28.7) form in diethyl ether solution an equilibrium mixture in which the [silane]/[silyl anion]
ratio is 12:7, corresponding to a pK value for (Me3Si)3SiH of 29.4.
Knowledge about the acidity of carbon acids1 is
fundamental to the understanding of a variety of
structure-reactivity relationships in organic chemistry.2
It also has practical consequences as it reflects the
stabilities of carbanions, key intermediates utilized in
a multitude of synthetic transformations of organic
molecules.2 While much effort has been devoted to
determining the thermodynamic3 and the kinetic4 acidi-


Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology


Collections: Chemistry