Invidious

Hello everyone, This post is regarding the question asked in relation to homoaromaticity in case of anions.

I read the comments and saw you all are not going in the right direction.

Structures having negative charge can also be a part of homoaromaticity eg. see the structure below having total of 10π electrons and aromaticity can be achieved by surpassing one sp3 C atom.

But there is lack of evidence for existence of such homoaromaticity as

1. MO calculations fail to establish it's stabilisation
2. Sometimes there is absence of diamagnetic current in NMR.
3. Substantial bond alteration is present.

You can refer Advanced F.A. Carey, Part A, Chapter: 8 Aromaticity, Pg 745 for one more example which has been studied in detail.

Here's the link of the video for those who have not seen it yet.
https://youtu.be/IM1hs54UqDU

Happy Learning!
Amit Bhandari
Team, J Chemistry