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Phenalene

From Wikipedia, the free encyclopedia
For the di-substituted benzene ring molecular fragment, seephenylene.
Phenalene
Ball-and-stick model of the phenalene molecule
Names
Preferred IUPAC name
1H-Phenalene
Other names
1-Benzonaphthene; 1H-Benzonaphthene; Perinaphthene; Perinaphthindene; peri-Naphthindene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.005.371Edit this at Wikidata
UNII
  • InChI=1S/C13H10/c1-4-10-6-2-8-12-9-3-7-11(5-1)13(10)12/h1-8H,9H2 checkY
    Key: XDJOIMJURHQYDW-UHFFFAOYSA-N checkY
  • InChI=1/C13H10/c1-4-10-6-2-8-12-9-3-7-11(5-1)13(10)12/h1-8H,9H2
    Key: XDJOIMJURHQYDW-UHFFFAOYAK
  • c3c1cccc2\C=C/Cc(c12)cc3
Properties
C13H10
Molar mass166.22 g/mol
Appearancewhite solid
Density1.139 g/cm3
Melting point159–160 °C (318–320 °F; 432–433 K)
Acidity (pKa)18.1 (inDMSO)[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

1H-Phenalene, often called simplyphenalene is apolycyclic aromatic hydrocarbon (PAH). Like many PAHs, it is an atmospheric pollutant formed during the combustion of fossil fuels.[2] It is the parent compound for the phosphorus-containingphosphaphenalenes.

The name was proposed by German chemists in 1922 as a contraction ofperiphenonaphthalene.[3]

Reactions

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Phenalene is deprotonated by potassium methoxide to give the phenalenyl anion.[4]

See also

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References

[edit]
  1. ^Bausch, M. J.; Guadalupe-fasano, C.; Jirka, G.; Peterson, B.; Selmarten, D. (1991-01-01). "Examinations of Dimethyl Sulfoxide-Phase Equilibrium Acidities of Selected Polycyclic Aromatic Compounds".Polycyclic Aromatic Compounds.2 (1):19–27.doi:10.1080/10406639108047854.ISSN 1040-6638.
  2. ^Gao H, Ma MQ, Zhou L, Jia RP, Chen XG, Hu ZD (2007). "Interaction of DNA with aromatic hydrocarbons fraction in atmospheric particulates of Xigu District of Lanzhou, China".J Environ Sci (China).19 (8):948–54.Bibcode:2007JEnvS..19..948G.doi:10.1016/S1001-0742(07)60156-9.PMID 17966851.
  3. ^Fritz Mayer and Adolf Sieglitz (1922)."Investigations and Ring Closures in the Series of the Methylnaphthalenes".Journal of the Chemical Society.122 (1–2).
  4. ^Reid, D. H. (1965-01-01). "The chemistry of the phenalenes".Quarterly Reviews, Chemical Society.19 (3): 274.doi:10.1039/qr9651900274.ISSN 0009-2681.
2 rings
3 rings
4 rings
5 rings
6 rings
7+ rings
General classes


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