* Electron Density and Resonance: Aniline (C6H5NH2) has a lone pair of electrons on the nitrogen atom that can participate in resonance with the aromatic ring. This delocalization of electrons stabilizes the ring but actually reduces the electron density on the nitrogen atom.
* Basicity: This reduced electron density on the nitrogen makes aniline less basic than ammonia. Ammonia has a more localized lone pair, making it a stronger base.
* Inductive Effect: The phenyl group in aniline has an electron-withdrawing inductive effect, further decreasing the electron density on the nitrogen.
In summary:
* Resonance and electron delocalization stabilize the aromatic ring in aniline but make the nitrogen less basic.
* Inductive effect of the phenyl group further reduces the electron density on the nitrogen.
Therefore, ammonia is more stable than aniline due to its higher electron density and stronger basicity.
