aniline

Question

Aniline is less basic than methylamine because:

RankGuru · Accepted Answer

**Aniline** is a weaker base than aliphatic amines (like methylamine) due to the **Resonance Effect**.
- In aniline ($C_6H_5NH_2$), the lone pair of electrons on the nitrogen atom is in conjugation with the $\pi$-electron system of the benzene ring.
- Through resonance, the electron density is delocalized over the ring, making the lone pair **less available** for coordination with a proton ($H^+$).
- Furthermore, the anilinium ion formed after protonation has fewer resonance structures than aniline itself, making it comparatively unstable. 
- Aliphatic amines have no such resonance and instead benefit from the $+I$ effect of the alkyl group.

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aniline

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