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Updated: May 8, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Communication: Infrared spectroscopy of protonated allyl-trimethylsilane: Evidence for the β-silyl effect
Barbara Chiavarino1, Maria Elisa Crestoni, Joel Lemaire
1Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma La Sapienza, P. le A. Moro 5, I-00185 Roma, Italy. barbara.chiavarino@uniroma1.it
Abstract:
β-trimethylsilyl-2-propyl cation has been formed by the gas phase protonation of allyl-trimethylsilane and characterized by infrared multiple photon dissociation spectroscopy. The experimental Cβ-Cα (+) stretching feature at 1586 cm(-1), remarkably blue-shifted with respect to a C-C single bond stretching mode, is indicative of high double bond character, a signature of β-stabilizing effect due to hyperconjugation of the trimethylsilyl group in the β-position with respect to the positively charged carbon. Density functional theory calculations at the B3LYP∕6-311++G(2df,2p) level yield the optimized geometries and IR spectra for candidate isomeric cations and for neutral and charged reference species.
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