Phenanthrene
From Wikipedia, the free encyclopedia
| Phenanthrene | |
|---|---|
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| IUPAC name | Phenanthrene |
| Identifiers | |
| CAS number | [85-01-8] |
| PubChem | |
| SMILES | c1ccc2c(c1)ccc3ccccc32 |
| InChI | 1/C14H10/c1-3- 7-13-11(5-1)9-10- 12-6-2-4-8-14(12)13/ h1-10H |
| Properties | |
| Molecular formula | C14H10 |
| Molar mass | 178.23 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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).
Contents |
[edit] 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, including:
- Organic oxidation to phenanthrenequinone with chromic acid [2]
- Organic reduction to[9,10-dihydrophenanthrene with hydrogen gas and raney nickel [3]
- Electrophilic halogenation to 9-bromophenanthrene with bromine [4]
- Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid [5]
- Ozonolysis to diphenylaldehyde [6]
[edit] 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.
[edit] References
- ^ chempensoftware.com Link
- ^ Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) Link
- ^ Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) Link.
- ^ Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) Link.
- ^ Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) Link.
- ^ Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) Link.
