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Pyridine
pi-electron poor
Nitrogen lone pair (not involved in ring)
Basic and nucleophilic
HBA

Pyrrole (NH), Furan (O), Thiophene (S) - have heteroatoms (N, O, S)
Pyrrole -
pi-electron rich
Nitrogen lone pair involved in ring
Acidic due to NH - HBD

Imidazole
1 N lone pair in ring, 1 N lone pair not in ring
HBA and HBD
pos/neg charged shared equally between N’s, therefore:
Stronger base than pyridine
Stronger acid than pyrrole
FOUND IN HISTIDINE - acts as either acid or base - important in enzyme catalysis
Draw penicillin


Pyrimidine

Purine

Quinoline

isoquinoline