Interactions | Reactions | Processes


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Classified as: Substitution: Nucleophilic Aromatic



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Nucleophilic aromatic substitution occurs when a nucleophilic Lewis base displaces a nucleofuge from an sp2 aromatic carbon. Aromatic systems are generally electron rich moieties in which the ¹-system inhibits the substitution. (The electron rich nucleophile has to pierce the electron rich pi-system to reach the centre at which the nucleophilic substitution is to occur.) However, if the Nfg function Ñfor example, a halogenÑ has electron withdrawing functions ortho or para to the Nfg, the reaction proceeds far more readily. Many halogenated nitrogen heterocycles are susceptible to SNAr attack.
  +  
H2O
        
  +  
N2
  +  
H+

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  +  
NaOH
        
  +  
Na+
  +  
[HSO3]–

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  +  
[OH]–
  +  
H2O
        
  +  
N2

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  +  
KOH
        
  +  
KCl

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  +  
2
NH3
  +  
CuCl
        
  +  
NH4Cl

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  +  
NH3
  +  
Al2O3
        
  +  
H2O

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© Mark R. Leach 1999 –

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