Misplaced Pages

Pentalene

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Pentalene
Names
Preferred IUPAC name Pentalene
Other names Bicyclooctatetraene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1/C8H6/c1-3-7-5-2-6-8(7)4-1/h1-6H
SMILES
  • C1=CC2=CC=CC2=C1
Properties
Chemical formula C8H6
Molar mass 102.136 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Pentalene is a polycyclic hydrocarbon composed of two fused cyclopentadiene rings. It has chemical formula C8H6. It is antiaromatic, because it has 4n π electrons where n is any integer. For this reason it dimerizes even at temperatures as low as −100 °C. The derivative 1,3,5-tri-tert-butylpentalene was synthesized in 1973. Because of the tert-butyl substituents this compound is thermally stable. Pentalenes can also be stabilized by benzannulation for example in the compounds benzopentalene and dibenzopentalene.

Dilithium pentalenide was isolated in 1962, long before pentalene itself in 1997. It is prepared from reaction of dihydropentalene (pyrolysis of an isomer of dicyclopentadiene) with n-butyllithium in solution and forms a stable salt. In accordance with its structure proton NMR shows 2 signals in a 2 to 1 ratio. The addition of two electrons removes the antiaromaticity; it becomes a planar 10π-electron aromatic species and is thus a bicyclic analogue of the cyclooctatetraene (COT) dianion C8H2−8.

Synthesis dilithium pentalenide

The dianion can also be considered as two fused cyclopentadienyl rings, and has been used as a ligand in organometallic chemistry to stabilise many types of mono- and bimetallic complexes, including those containing multiple metal-metal bonds, and anti-bimetallics with extremely high levels of electronic communication between the centers.

See also

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 209. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Hopf, Henning (2013). "Pentalenes-From Highly Reactive Antiaromatics to Substrates for Material Science". Angewandte Chemie International Edition. 52 (47): 12224–6. doi:10.1002/anie.201307162. PMID 24127399.
  3. Carey, Francis A.; Sundberg, Richard J. (1984). Advanced Organic Chemistry: Part A Structure and Mechanisms (2nd ed.). New York, NY: Plenum Press. ISBN 0-306-41198-9.
  4. Bally T.; Chai S.; Neuenschwander M.; Zhu Z. (1997). "Pentalene: Formation, Electronic, and Vibrational Structure" (PDF). J. Am. Chem. Soc. 119 (8): 1869–1875(7). doi:10.1021/ja963439t. Archived from the original (reprint) on 2007-03-15. Retrieved 2007-07-06.
  5. Hafner, K.; Süss, H. U. (1973). "1,3,5-Tri-tert-Butylpentalene. A Stabilized Planar 8π-Electron System". Angew. Chem. Int. Ed. Engl. 12 (7): 575–577. doi:10.1002/anie.197305751.
  6. Katz, Thomas J.; Rosenberger, Michael. (1962). "The Pentalenyl Dianion". Journal of the American Chemical Society. 84 (5): 865. doi:10.1021/ja00864a038.
  7. Summerscales, Owen T.; Cloke, F. Geoffrey N. (2006). "The organometallic chemistry of pentalene". Coordination Chemistry Reviews. 250 (9–10): 1122. doi:10.1016/j.ccr.2005.11.020.
Categories: