Question

Which is more basic?

Answer 1

The structures are shown in the image$.$

The lone electrons of $N$ in pyrrole is delocalized $.$ It is part of the $Pi$ system$,$ thus involved in aromatization $.$ This $L.P$ is no longer available for a proton hence it is a weak base$.$

One the other hand$,$ aniline is already aromatic$.$ Through the lone pair of $e^{-}$ of $-N{H}_2$ group of aniline is delocalized over the benzene ring$,$ it is not involved in aromatizetion $.$ This pair of lone electron still available for a proton$,$ hence aniline is stronger base than pyrrole$.$