Prismane
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Preferred IUPAC name
Tetracyclo[2.2.0.02,6.03,5]hexane
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| Other names
Prismane (no longer recommended)
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3D model (Jmol)
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| Properties | |||
| C6H6 | |||
| Molar mass | 78.11 g·mol−1 | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Prismane 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. The compound was not synthesized until 1973.
In the mid 19th century, investigators proposed several possible structures for benzene which were consistent with its empirical formula, C6H6, which had been determined by combustion analysis. The first, which was proposed by Kekulé in 1865, later proved to be closest to the true structure of benzene. This structure inspired several others to propose structures that were consistent with benzene's empirical formula; for example, Ladenburg proposed prismane, Dewar proposed Dewar benzene, and Koerner and Claus proposed Claus' benzene. Some of these structures would be synthesized in the following years. Prismane, like the other proposed structures for benzene, is still often cited in the literature, because it is part of the historical struggle toward understanding the mesomeric structures and resonance of benzene. Some computational chemists still research the differences between the possible isomers of C6H6.
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