Cuneane
Saturated hydrocarbon compound (C8H8)
From Wikipedia, the free encyclopedia
Cuneane (from Latin cuneus 'wedge'[1]) is a saturated hydrocarbon with the formula C8H8 and a 3D structure resembling a wedge, hence the name. Cuneane may be produced from cubane by metal-ion-catalyzed σ-bond rearrangement.[2][3] Similar reactions are known for homocubane (C9H10) and bishomocubane (C10H12).[4][5]
Synthesis of cuneane from cubane
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| Names | |
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| Preferred IUPAC name
Pentacyclo[3.3.0.02,4.03,7.06,8]octane | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C8H8 | |
| Molar mass | 104.152 g·mol−1 |
| Density | 1.578 g/ml |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Molecular geometry
The carbon atoms in the cuneane molecule form a hexahedron with point group C2v. The cuneane molecule has three kinds of equivalent carbon atoms (A, B, C), which have also been confirmed by NMR.[6] The molecular graph of the carbon skeleton of cuneane is a regular graph with non-equivalent groups of vertices, and so it is a very important test object for different algorithms of mathematical chemistry.[7][8]
Equivalent carbon atoms in cuneane
Derivatives
Some cuneane derivatives have liquid crystal properties.[9]