On Tue, Oct 23, 2018 at 4:08 PM Peter S. Shenkin <shen...@gmail.com> wrote:

>
>    - Easily understandable explanation:
>       - From the Daylight theory manual (and you've used similar
>       language): *exocyclic double bonds do not break aromaticity.*
>       - I'd alter this to *double bonds exocyclic to the ring in question
>       do not break aromaticity*. (I.e., even if they are in other rings)
>       - Beyond this, conventional electron counting explains everything
>       in Francis's example and mine.
>    -
>
> You're close, but I think there's something missing.
Exocyclic double bonds do not prevent an atom from being considered
aromatic, but they *may* "steal" a pi-electron - e.g. the C that's double
bonded to the O in pyridone contributes zero electrons to the aromatic
ring. The challenge here is to define which exocyclic double bonds can do
this.

For example, you guys are agreeing that the N exocyclic bond next to the
boxed C here:
[image: image.png]
does remove an electron.

and, to go all the way in the other direction, what happens here:
[image: image.png]
And here:
[image: image.png]
Is that left ring aromatic in all cases? If not, why not?

-greg
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