Is there any sort of resonance in this ion?

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1 Answer
Dec 3, 2017

Yes,there is resonance in this ion.

But it isn't the type you may be thinking of.

It is just the normal resonance involving the two Kekulé forms of benzene.

www.kentchemistry.comwww.kentchemistry.com

It doesn't involve the lone pair of electrons on the carbon atom.

C6H5-C6H5-

If you think about it, you will realize that the anion was formed by removal of a proton like the one indicated in the picture below.

sp2sp2
(Adapted from jayzeetee.wordpress.com)

The lone pair is in an #"sp"^2# orbital. which is orthogonal to the π orbital system of the ring.

That means there in no interaction between them

If the major lobe of the #"sp"^2# orbital is "red"", any overlap with the "red" portion of the π orbital above the ring is cancelled by the overlap with the "blue" portion below the ring.

There is no net interaction and therefore no resonance involvement of the #"sp"^2# orbital with the π system of the ring.