In my textbook, as examples of delocalization of pi electrons, benzene and nitrate ion have been considered. Benzene, due to symmetry of its resonating structures is simple enough. We assume that σ electrons are localized and π electrons are delocalized in the ring.
Each carbon atom promotes one electron from its s orbital to the empty 2p orbital. It hybridizes two p orbitals with the s to form three sp2 orbitals which it then uses to form three σ bonds, two with other carbons and one with a hydrogen.
The remaining unhybridized p orbital then sticks out above and below the plane of the ring. The electrons from all the six unhybridized p orbitals of the six carbons are then delocalized above and below the plane of the ring.
However, when I try to apply a similar reasoning to the nitrate anion, problems arise. The resonating lewis structures of nitrate ions are:
Now, assuming again that only the π electrons are delocalized, we would expect that only 2 electrons are delocalized (since there is only one double bond). But my textbook claims that each atom is sp2 hybridized, and as in benzene, one unhybridized p orbital per atom sticks out above and below the plane of the molecule.
Assuming this to be true, I presumed that two electrons would be localized ans tried to arrange the remaining 22 electrons into a lewis structure with sp2 hybridized atoms. I couldn't find any viable structure with only three lone pairs around each atom. What is the exact mechanism for delocalization of electrons in nitrate? Is there a general scheme to this mechanism that applies to all such similar molecules (COX3X2− for instance)?
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