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Topic: does anybody know why silicon can stabilize beta cations?  (Read 3790 times)

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Offline g-bones

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does anybody know why silicon can stabilize beta cations?
« on: April 07, 2008, 01:01:29 AM »
does anybody know why silicon can stabilize beta cations? any help or references would help?

Offline Rico

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Re: does anybody know why silicon can stabilize beta cations?
« Reply #1 on: April 07, 2008, 06:44:04 AM »
Hey g-bones

The stabilization of beta-cations by silicon can be explained by an overlap of the C-Si sigma bonding orbital and the empty p-orbital in the cation, the C-Si sigma bonding orbital donating electrons to the empty p-orbital (see jpeg attached). Two reasonable resonance-structures can also be drawn, the first one of course the most contributing one, since the C-Si bond is not broken, but some positive charge will reside on silicon.

I hope this answers your question.

Rico

Offline g-bones

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Re: does anybody know why silicon can stabilize beta cations?
« Reply #2 on: April 07, 2008, 04:29:23 PM »
great thanks man, i was thinking it was hyperconjugation as well just couldnt quite picture it.  great job putting into "understandable" format haha

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