Aromatic Heterocyclic Compounds

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Presentation transcript:

Aromatic Heterocyclic Compounds

Aromatic Five-Membered Heterocycles

Pyrrole is an extremely weak base

Pyrrole Also aromatic, but lone pair of electrons is delocalized, so much weaker base. =>

5-membered ring system 29

Other Heterocyclics =>

Other Heterocyclics indole benzofuran benzothiophene

Aromatic Six-Membered-Ring Heterocycles

Heterocyclic aromatic compound. Pyridine Heterocyclic aromatic compound. Nonbonding pair of electrons in sp2 orbital, so weak base, pKb = 8.8. =>

The pyridinium ion is a stronger acid than a typical ammonium ion

Quinoline and isoquinoline are known as benzopyridines

Some Biologically Important Heterocycles Imidazole

Some Biologically Important Heterocycles

Pyrimidine has two basic nitrogens. Basic or Nonbasic? Pyrimidine has two basic nitrogens. Imidazole has one basic nitrogen and one nonbasic. Purine? =>

Chlorophyll a

Porphyrin

BILE PIGMENTS (bilirubin and biliverdin) H e m v d N C O 3 2 - D A x a t on R c F + ,

Gallstones (bilirubin) Collection of Pathological Department

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