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Prismane information


Prismane
Chemical structure of prismane
Chemical structure of prismane
Chemical structure of prismane
Chemical structure of prismane
CPK model of prismane
Names
Preferred IUPAC name
Tetracyclo[2.2.0.02,6.03,5]hexane[1]
Identifiers
CAS Number
  • 650-42-0 checkY[PubChem]
3D model (JSmol)
  • Interactive image
ChemSpider
  • 16736515 checkY
PubChem CID
  • 12305738
CompTox Dashboard (EPA)
  • DTXSID90486733 Edit this at Wikidata
InChI
  • InChI=1S/C6H6/c1-2-3(1)6-4(1)5(2)6/h1-6H checkY
    Key: RCJOMOPNGOSMJU-UHFFFAOYSA-N checkY
  • InChI=1/C6H6/c1-2-3(1)6-4(1)5(2)6/h1-6H
    Key: RCJOMOPNGOSMJU-UHFFFAOYAA
SMILES
  • C12C3C1C4C2C34
Properties
Chemical formula
C6H6
Molar mass 78.114 g·mol−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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Infobox references

Prismane or 'Ladenburg benzene' is a polycyclic hydrocarbon with the formula C6H6. It is an isomer of benzene, specifically a valence isomer. Prismane is far less stable than benzene. The carbon (and hydrogen) atoms of the prismane molecule are arranged in the shape of a six-atom triangular prism—this compound is the parent and simplest member of the prismanes class of molecules. Albert Ladenburg proposed this structure for the compound now known as benzene.[2] The compound was not synthesized until 1973.[3]

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2013. p. 169. doi:10.1039/9781849733069-00130. ISBN 978-0-85404-182-4. The name prismane is not longer recommended.
  2. ^ Ladenburg A. (1869). "Bemerkungen zur aromatischen Theorie" (PDF). Chemische Berichte. 2: 140–2. doi:10.1002/cber.18690020171.
  3. ^ Katz T. J.; Acton N. (1973). "Synthesis of Prismane". Journal of the American Chemical Society. 95 (8): 2738–2739. doi:10.1021/ja00789a084.

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Prismane

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Prismane or 'Ladenburg benzene' is a polycyclic hydrocarbon with the formula C6H6. It is an isomer of benzene, specifically a valence isomer. Prismane...

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The prismanes are a class of hydrocarbon compounds consisting of prism-like polyhedra of various numbers of sides on the polygonal base. Chemically, it...

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graphene. Phagraphene: Graphene-like allotrope with distorted Dirac cones. Prismane C8 is a theoretically predicted metastable carbon allotrope comprising...

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C6H6

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Benzvalene Bicyclopropenyl 1,2,3-Cyclohexatriene Dewar benzene Fulvene Prismane [3]Radialene 3-Methylidenepent-1-en-4-yne Hexadiyne 1,3-Hexadiyne 1,4-Hexadiyne...

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substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole. Before...

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Organotin chemistry

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tristannylene [Sn(C6H3-2,6-Et2)2]3, which affords the cubane-type cluster and a prismane. These cages contain Sn(I) and have the formula [Sn(C6H3-2,6-Et2)]n where...

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hydrogen atoms cyclopentane, allene, 2-butyne, hexamethylenetetramine, prismane, cubane, dodecahedrane, etc. On the other hand, the hydrogen atoms of propane...

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Albert Ladenburg

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His proposed structure was eventually realised in 1973 in the molecule prismane. Ladenburg visited England, and then went on to work for 18 months in Paris...

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Aliphatic compound

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Mesitylene

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Albert Ladenburg in 1874; however, assuming wrong benzene structure of prismane. Historical mesitylene structures Mesitylene by Adolf von Baeyer (tetracyclo[3...

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Adolf Karl Ludwig Claus

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place in organic chemistry. Ladenburg's prismane and Claus' benzene were both proven to be wrong. While the prismane was synthesized in 1973, calculations...

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Fullerene

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Schultz, H.P. (1965). "Topological Organic Chemistry. Polyhedranes and Prismanes". Journal of Organic Chemistry. 30 (5): 1361–1364. doi:10.1021/jo01016a005...

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Dewar benzene

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alongside other classic structures such as the isomers prismane, benzvalene and Claus' benzene. Prismane and benzvalene were synthesized in the 1970s; Claus'...

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