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Wednesday, January 22, 2020

Why pyridine is more basic than Pyrrole?

In case of Pyrrole  the lone pair electrons of the nitrogen atom is involved in conjugated system of pi electrons of five membered ring leading to greater stability of the molecule due to acquiring aromatic character. Hence less available for donation.
While in case pyridine already has a stable conjugated system of three double bonds in an aromatic ring, like benzene. Hence the lone pair electrons on the N atom in pyridine is localized and  more available for donation and  easily donated to a H+ ions. Therefore, pyridine is a stronger base than Pyrrole.

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