Cubane
Organic compound (C8H8) with a cube carbon structure / From Wikipedia, the free encyclopedia
Cubane is a synthetic hydrocarbon compound with the formula C8H8. It consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline 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.[4] Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles".[5][6] The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry.
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
Cubane[1] | |||
Systematic IUPAC name
Pentacyclo[4.2.0.02,5.03,8.04,7]octane | |||
Identifiers | |||
| |||
3D model (JSmol) |
|||
ChEBI | |||
ChemSpider |
| ||
PubChem CID |
|||
UNII | |||
CompTox Dashboard (EPA) |
|||
| |||
| |||
Properties | |||
C8H8 | |||
Molar mass | 104.15 g/mol | ||
Appearance | Transparent[2] crystalline solid | ||
Density | 1.29 g/cm3 | ||
Melting point | 133.5 °C (272.3 °F; 406.6 K)[3] | ||
Boiling point | 161.6 °C (322.9 °F; 434.8 K)[3] | ||
Related compounds | |||
Related hydrocarbons |
Cuneane Dodecahedrane Tetrahedrane Prismane Prismane C8 | ||
Related compounds |
Octafluorocubane Octanitrocubane Octaazacubane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Having high potential energy and kinetic stability makes cubane and its derivative compounds useful for controlled energy storage. For example, octanitrocubane and heptanitrocubane have been studied as high-performance explosives. These compounds also typically have a very high density for hydrocarbon molecules. The resulting high energy density means a large amount of energy can be stored in a comparably smaller amount of space, an important consideration for applications in fuel storage and energy transport. Furthermore, their geometry and stability make them suitable isosteres for benzene rings.[7]