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Define negative hyperconjugation, provide an example for a silicon-containing molecule featuring negative hyperconjugation, and draw a...

Define negative hyperconjugation, provide an example for a silicon-containing molecule featuring negative hyperconjugation, and draw a diagram showing the orbitals involved in this interaction.

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Answer #1

negative hyperconjugation is the donation of electron density from a filled π- or p-orbital to a neighboring σ*-orbital. This phenomenon, a type of resonance, can stabilize the molecule or transition state.It also causes an elongation of the σ-bond by adding electron density to its antibonding orbital.

In negative hyperconjugation, the electron density flows in the opposite direction (from π- or p-orbital to empty σ*-orbital) than it does in the more common hyperconjugation (from σ-orbital to empty p-orbital)

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