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Aromatic Heterocyclic Compounds. Aromatic Five-Membered Heterocycles.

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Presentation on theme: "Aromatic Heterocyclic Compounds. Aromatic Five-Membered Heterocycles."— Presentation transcript:

1 Aromatic Heterocyclic Compounds

2 Aromatic Five-Membered Heterocycles

3 Pyrrole is an extremely weak base

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

5 29 5-membered ring system

6 Other Heterocyclics =>

7 indolebenzofuran benzothiophene Other Heterocyclics

8 Aromatic Six-Membered-Ring Heterocycles

9 Pyridine Heterocyclic aromatic compound. Nonbonding pair of electrons in sp 2 orbital, so weak base, pK b = 8.8. =>

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

11 Quinoline and isoquinoline are known as benzopyridines

12 Some Biologically Important Heterocycles Imidazole

13 Some Biologically Important Heterocycles

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

15 Chlorophyll a

16 Porphyrin

17 BILE PIGMENTS (bilirubin and biliverdin) Bilirubin H Hem Biliverdin NNN N C CCO O H 3 CC CH 2 H 3 CCH 2 C CH 2 COO - C C CH 3 CCH CH 2 HH H - OO H 2 H 2 H 3 H H H HH BC D A A D CB HH H H H H H 3 H 2 H 2 - OO H NNN N C CCO O H 3 CC CH 2 H 3 CCH 2 C CH 2 COO - C C CH 3 CCH CH 2 Oxidation Reducti -Fe 3+, -CO

18 Gallstones (bilirubin) Collection of Pathological Department

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