Aniline, with five resonating structures, is more stable than the anilinium ion, which has only two resonating structures (kekule). The greater stability of aniline contributes to its lower proton acceptability or basic nature compared to ammonia.
Explain the relationship between the number of resonating structures and the stability of aniline, comparing it to the anilinium ion.
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The stability of aniline is enhanced by resonance, allowing for the delocalization of the lone pair on nitrogen into the aromatic ring. Aniline has two major resonance structures, distributing the positive charge among different atoms in the ring. In contrast, the anilinium ion (C₆H₅NH₃⁺) lacks this delocalization, having only one significant resonance structure. The presence of multiple resonating structures in aniline increases its stability compared to the anilinium ion. Resonance stabilization in aniline contributes to its lower basicity and higher stability, as it disperses the positive charge more effectively across the aromatic ring.