Prismane

Prismane
Chemical structure of prismane	Chemical structure of prismane
Names
	Preferred IUPAC name Tetracyclo[2.2.0.02,6.03,5]hexane
Identifiers
CAS Number	650-42-0 [PubChem];
3D model (JSmol)	Interactive image;
ChemSpider	16736515 ;
PubChem CID	12305738;
CompTox Dashboard (EPA)	DTXSID90486733 ;
	InChI InChI=1S/C6H6/c1-2-3(1)6-4(1)5(2)6/h1-6H Key: RCJOMOPNGOSMJU-UHFFFAOYSA-N ; 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). verify (what is ?) 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]

^ 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.
^ Ladenburg A. (1869). "Bemerkungen zur aromatischen Theorie" (PDF). Chemische Berichte. 2: 140–2. doi:10.1002/cber.18690020171.
^ Katz T. J.; Acton N. (1973). "Synthesis of Prismane". Journal of the American Chemical Society. 95 (8): 2738–2739. doi:10.1021/ja00789a084.

[iupac2013-1] 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.

[1]

[2]

[3]