Wednesday, January 9, 2019

orbitals - Why can't the conjugate base of benzoic acid be stabilized by conjugation with the aromatic ring?


All the carbon and oxygen atoms are sp2 hybridised and can have a p orbital in the correct plane yet only conjugation of the COO- group occurs. I can't think why. I can't draw resonance structures for the negative charge being delocalised around the ring but if you look at it from the orbital perspective (sp2 hybridisation) it seems clear that this conjugation should occur.




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