AAMC and Nitrogen hybridization

[Necr0sis713]

Advertisement - Members don't see this ad

I was just curious. I noticed that some practice material consider a conjugated nitrogen to be Sp2 hybridized, while some other companies consider it straight Sp3.

Does anyone have any idea what the AAMC would consider such a nitrogen? Like a nitrogen in an aromatic system.

 

[betterfuture]

This is what I know.

In the case with pyridine, a biologically important molecule, the 6 membered ring is aromatic since it is cyclic, planar and completely conjugated and satisfies Huckels rule. The N is sp2 hybridized. Since it has one unhybridized p orbital it overlaps with adjacent p orbitals to make the ring conjugated but the lone pairs do not participated in the delocalization of the electrons.

Pyrrole is also aromatic and the N is sp2 hybridized and it also has a p unhybridized orbital. The lone pair on N participates in the conjugation of the system giving it 6 pi electrons and if it didn't the ring would not satisfy Huckel's rule.