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Aromatic Heterocyclic Compounds

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Presentation on theme: "Aromatic Heterocyclic Compounds"— 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 5-membered ring system 29

6 Other Heterocyclics =>

7 Other Heterocyclics indole benzofuran benzothiophene

8 Aromatic Six-Membered-Ring Heterocycles

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

13 Some Biologically Important Heterocycles

14 Pyrimidine has two basic nitrogens.
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)
H e m v d N C O 3 2 - D A x a t on R c F + ,

18 Gallstones (bilirubin)
Collection of Pathological Department

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