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Aromatic Heterocyclic Compounds. Aromatic Five-Membered Heterocycles

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Aromatic Heterocyclic Compounds Slide 2 Aromatic Five-Membered Heterocycles Slide 3 Pyrrole is an extremely weak base Slide 4 Pyrrole Also aromatic, but lone pair of electrons is delocalized, so much weaker base. => Slide 5 29 5-membered ring system Slide 6 Other Heterocyclics => Slide 7 indolebenzofuran benzothiophene Other Heterocyclics Slide 8 Aromatic Six-Membered-Ring Heterocycles Slide 9 Pyridine Heterocyclic aromatic compound. Nonbonding pair of electrons in sp 2 orbital, so weak base, pK b = 8.8. => Slide 10 The pyridinium ion is a stronger acid than a typical ammonium ion Slide 11 Quinoline and isoquinoline are known as benzopyridines Slide 12 Some Biologically Important Heterocycles Imidazole Slide 13 Some Biologically Important Heterocycles Slide 14 Basic or Nonbasic? Pyrimidine has two basic nitrogens. Imidazole has one basic nitrogen and one nonbasic. Purine? => Slide 15 Chlorophyll a Slide 16 Porphyrin Slide 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 Slide 18 Gallstones (bilirubin) Collection of Pathological Department

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