Explain in detail why methyl amine is a stronger base than aniline

Question

Answer should focus on both the ground state and the conjugate acod state

Answer 1

Basic strength of a lewis base (in general) depends on how easily the lone pair of electrons can be donated. Higher the density of negative charge on the nitrogen, stronger will be the base. In aniline, the lone pair is involved in resonance with the benzene ring and hence is delocalized. In other words, the lone pair is not easily available to the proton (say). In methyl amine, the lone pair is localized and hence easily available. Moreover, methyl amine is much less sterically hindered compared to aniline.

Answer 2

When aniline accepts the H, it loses its resonance so is less stable, while the methyl amine can accept another H because of its lone pair.  I completely forgot if it even has a lone pair, so double check that.