Why is aniline less basic than methylamine?
N in aniline is forced into an $\ce{sp^2}$ configuration because only then can its p orbital interact to form aromatic MO’s. By contrast, methylamine has its N in the usual $\ce{sp^3}$ configuration. An $\ce{sp^2}$ lone pair has a great contribution from an s AO than an $\ce{sp^3}$ lone pair (33% vs 25%), and because an s AO is lower in energy than a p AO (due to a region of electronic density closer to the nucleus), it is also lower in energy. Therefore, the HOMO of aniline has a poorer energy match with the H 1s LUMO than the HOMO of methylamine, and the resonance energy stabilizing the protonated adduct is smaller. Hence, aniline is less basic.