Aniline template

PhNH₂: the neutral form and three charge-separated forms with N⁺ and the negative charge on the ortho, para and other ortho carbons.

What the template shows

• The nitrogen lone pair is delocalised into the ring
• Resonance contributors
• Negative charge: ortho, para, ortho′
• The neutral form is the major contributor; the charge-separated forms show where the ring is electron-rich.
• NH₂ is a strongly activating ortho/para director in electrophilic aromatic substitution (aniline and Br₂ water give 2,4,6-tribromoaniline).
• The lone pair is less available for protons, so aniline (pKaH 4.6) is a much weaker base than cyclohexylamine (pKaH 10.6).
• Contributors are not in equilibrium: the real species is one hybrid of them · every part of this figure is editable

Drawn with 28 atoms, 9 arrows, 2 shapes – every one editable in MolDraw.

Sources

• Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 7 Textbook
• Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020 Textbook