Question

write a resonance form for pyrrole in which nitrogen has a formal charge of 1. are comparable resonance forms possible for pyridine? be sure to include all lone pair electrons in your drawing.

Answer 1

The pyridine and pyrrole structures both have nitrogen atoms with +1 formal charge.

Now, we can observe that the nitrogen atom in the heterocycle has a formal charge of +1 in the resonance forms of pyrrole. However, as illustrated in the attached canonical structures, the nitrogen atom in the six-membered pyridine hetrocycle may have a formal charge of +1 or -1. Similar to structures made from pyrrole, pyridine structures have nitrogen atoms with a positive formal charge. These structures don't contribute as much to the pyridine structure.

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