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Author: Subject: Homoaromaticity
Bedlasky
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[*] posted on 10-1-2021 at 10:56
Homoaromaticity


Hi.

I read about something called "homoaromaticity" today. It's similar to aromaticity, but the conjugated system of electrons is somewhat "disrupted" by another carbon. p orbitals are still close enough to overlap each other, so system of delocalized electrons is preserved, but you have carbon outside of this system. Look at this for better understanding:

https://en.wikipedia.org/wiki/Homoaromaticity

Adamantane form cations in superacidic systems, which are homoaromatic and also contain quite unusual four-centred-two electron bond:

https://en.wikipedia.org/wiki/Adamantane#Adamantane_cations

https://en.wikipedia.org/wiki/Four-center_two-electron_bond




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