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Phenanthrene



Phenanthrene
IUPAC name phenanthrene
Identifiers
CAS number 85-01-8
PubChem 995
InChI InChI=1/C14H10/c1-3-
7-13-11(5-1)9-10-
12-6-2-4-8-14(12)13/
h1-10H
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings--as the above formula shows. 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.

Additional recommended knowledge

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

Chemistry

A classical phenanthrene synthesis is the Bardhan-Sengupta Phenanthrene Synthesis (1932) [1]. 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. Some basic reactions:

Canonical forms of Phenanthrene

Phenanthrene has five resonance structures, given below:


The third and fourth rnce structures appear to be the same; they are in fact just 180° rotations of each other, as the molecule is planar. However, they do deserve to be treated as separate structures, as what matters are the bonds on the individual carbon atoms, which remain fixed even when we rotate our frame of reference.

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.

More information on phenanthrene is available [1] [2].

References

  1. ^ chempensoftware.com Link
  2. ^ Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) Link
  3. ^ Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) Link.
  4. ^ Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) Link.
  5. ^ Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) Link.
  6. ^ Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) Link.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phenanthrene". A list of authors is available in Wikipedia.
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