Question

Why pyridine is stronger base compare to pyrrole?

Answer 1

Why is pyridine more basic than pyrrole?

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Kumaraswami Sathiavasan, MSc in Chemistry & IAS officer(retd.)

Updated Jun 15, 2016

In pyrrole, the lone pair electrons of the nitrogen atom is actively involved with the two carbon-carbon double bonds in the 5-member ring to form a conjugated system of pi electrons, leading to greater stability of the molecule.

Pyridine, on the other hand, already has a stable conjugated system of 3 double bonds in the aromatic hexagonal ring, like benzene. Hence the lone pair electrons on the N atom in pyridine can be easily donated to a H+ ion or a Lewis acid.
Therefore, pyridine is a stronger base than pyrrole