Phenalene

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Phenalene
Phenalene.svg
Phenalene molecule ball.png
Names
Preferred IUPAC name
1H-Phenalene
Other names
1-Benzonaphthene; 1H-Benzonaphthene; Perinaphthene; Perinaphthindene; peri-Naphthindene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.371 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C13H10/c1-4-10-6-2-8-12-9-3-7-11(5-1)13(10)12/h1-8H,9H2 Yes check.svgY
    Key: XDJOIMJURHQYDW-UHFFFAOYSA-N Yes check.svgY
  • 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 mass 166.22 g/mol
Appearancewhite solid
Density 1.139 g/cm3
Melting point 159–160 °C (318–320 °F; 432–433 K)
Acidity (pKa)18.1 (in DMSO) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1H-Phenalene, often called simply phenalene is a polycyclic 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-containing phosphaphenalenes.

Contents

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

Reactions

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

See also

Related Research Articles

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References

  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. 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.