Phenanthrene

Phenanthrene

[fuh-nan-threen]

Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name phenanthrene is a composite of phenyl and anthracene. It provides the framework for the Steroids. In its pure form, it is found in cigarette smoke and is a known irritant, photosensitising skin to light.

The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 position is known as phenanthroline or 4,5-diazaphenanthrene (IUPAC name).

Chemistry

A classical phenanthrene synthesis is the Bardhan-Sengupta Phenanthrene Synthesis (1932). In the second step of this reaction 9,10-dihydrophenanthrene is oxidized with elemental selenium. Phenanthrene can also be obtained photochemically from certain diarylethenes.

Reactions of phenanthrene typically occur at the 9 and 10 positions, including:

Canonical forms

Phenanthrene is more stable than its linear isomer anthracene. A classic and well established explanation is based on Clar's rule. A novel theory invokes so-called stabilizing hydrogen-hydrogen bonds between the C4 and C5 hydrogen atoms.

Natural occurrence

Ravatite is a natural analogue of (synthetic) phenanthrene. It was found in little amounts among few burning coal sites. Ravatite represents a small group of organic minerals.

References

External links

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