Chemistry - Is nitrogen of aniline sp² or sp³ hybridized?

The nitrogen in aniline is somewhere between $\mathrm{sp^3}$ and $\mathrm{sp^2}$ hybridized, probably closer to the $\mathrm{sp^2}$ side. We are correctly taught that the nitrogen in simple aliphatic amines is pyramidal ($\mathrm{sp^3}$ hybridized). However in aniline, due to the resonance interaction between the aromatic ring and the nitrogen lone pair, considerable flattening of the nitrogen occurs (if it were completely flat it would be $\mathrm{sp^2}$ hybridized).

We can assess the nitrogen hybridization by measuring its barrier for pyramidal inversion. If a trigonal nitrogen is $\mathrm{sp^2}$ hybridized, the barrier will be zero. On the other hand, in aliphatic amines where the nitrogen is $\mathrm{sp^3}$ hybridized the inversion barrier is typically around $\pu{4-5 kcal/mol}$.

pyramidal inversion diagram

(pyramidal inversion diagram)

In aniline this barrier is very low, somewhere around $\pu{1-2 kcal/mol}$. This indicates that the nitrogen in aniline is not quite planar, but is much closer to being planar ($\mathrm{sp^2}$) than pyramidal ($\mathrm{sp^3}$).

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Resonance