The compound 2,6-dimethyl-N,N-dimethylaniline is observed to be a substantially stronger base than s — Amines Chemistry Question

💡 Solution & Explanation

In 2,6-dimethyl-N,N-dimethylaniline, severe steric clash between the ortho methyl groups and the N-methyl groups forces the bulky $-N(CH_3)_2$ moiety to twist completely out of the benzene ring's plane. This physical twist (Steric Inhibition of Resonance) prevents lone pair delocalization, localizing electron density on nitrogen and massively boosting basicity.