Problem in aromatization

When you run Bonds --> Aromatize on the attached molecule, the structure ends up wrongly with non-aromatic ring getting aromatized. Is there a solution? Thanks,





Sumathy

Which ring should not be aromatized?


I have attached the aromatized form. Two 6 membered and one 5 membered ring is aromatized.


It seems to be correct for me.





Andras

Thanks for the reply. Sorry but I dont understand how one of the 6 membered ring containing 2 N and a out-of-the-ring O can get aromatized? Doesn't it violate the valence rule for the carbon (with its double bonded Oxygen and two single ring bonds)? Thanks,





Sumathy

Please check the following documentation:


http://www.chemaxon.com/marvin/doc/user/aromatization-doc.html





If something still not clear, please don't hesitate to ask for more help.





Andras

Dear Andras,





Thanks again for the attachments which clearly explain what is happening. I still want to understand the issue with 9-hydroxyrisperidone (9HR). The closest one to 9HR is pyridin-2(1H)-one. Still, there is a major difference that a ring is attached to one of the N and a C here. Will this not change the aromaticity of this molecule? I guess, Iam trying to understand if we are justified in applying the 'General aromaticity rule' for this molecule?





Regards,


Sumathy

Quote:

The closest one to 9HR is pyridin-2(1H)-one. Still, there is a major difference that a ring is attached to one of the N and a C here. Will this not change the aromaticity of this molecule?

If a ring is aromatic alone and you attach something to it (like an other ring) without changing the hybridization state of the atoms in the ring, then the ring keeps its aromaticity.





If you aromatize a molecule, you use 'General aromaticity detection' as this is the default method. You can also use the other method through the API or with specific options.





Andras