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Annulenes, Heterocyclic and Polycyclic Aromatic Compounds

Polycyclic Aromatic Compounds

Strictly speaking, the Hückel rule can only be applied to monocyclic compounds though the general concept may also be transferred to polycyclic molecules, such as polycyclic aromatic compounds. These compounds are actually considerably relevant. Benzo[e]pyrene, for instance, which is found in tobacco smoke, is suspected to be carcinogenic.

Fig.1
Fig.2

The formal condensation of a third benzene ring to naphthalene yields anthracene and phenanthrene, respectively. Anthracene and phenanthrene are isomers. However, anthracene is about 25 kJ/mol more stable than phenanthrene.

Examples of some important polycyclic aromatic compounds

Exercises

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