Nitrobenzene template

PhNO₂: a ring π bond forms C=N as the N=O π bond moves onto O, leaving δ+ on the ortho, para and other ortho carbons.

What the template shows

• The nitro group pulls π electrons out of the ring: positive charge at ortho and para
• Resonance contributors
• Positive charge: ortho, para, ortho′
• The neutral-ring form is the major contributor; the others show electron density pulled from ortho and para.
• NO₂ deactivates the ring and directs electrophiles meta: the meta carbons are the least electron-poor.
• The same withdrawal activates ortho/para halides to nucleophilic aromatic substitution (SNAr).
• The nitro group itself also has two equivalent N–O forms (see Nitro group).
• Contributors are not in equilibrium: the real species is one hybrid of them · every part of this figure is editable

Drawn with 36 atoms, 7 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