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Topic: Cyclopentadienyl Anion Aromaticity  (Read 10903 times)

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Offline mrlucky0

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Cyclopentadienyl Anion Aromaticity
« on: February 02, 2008, 01:50:28 AM »
Can someone explain why the Cyclopentadienyl anion is aromatic? My textbook says that the carbon with the lone pair is sp2 hybridized but I very difficult time understanding why. Here's what I am thinking

The negatively charged carbon has 4 electron regions: the H bond, the 2 carbon bonds, and the lone pair. Doesn't this make it sp3 hybridized?


Offline Yggdrasil

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Re: Cyclopentadienyl Anion Aromaticity
« Reply #1 on: February 02, 2008, 08:20:46 AM »
Very often sp3 hybridized atoms with lone pairs will change their hybridization to sp2 in order to allow for the molecule to become aromatic.  Even though the sp2 geometry does not allow for maximum separation of the electron regions, the stability gained from aromaticity greatly outweighs this slight increase in electrostatic strain.

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