Dodecahedrane
 |
|||
|
|||
| Names | |||
|---|---|---|---|
|
IUPAC name
[5]fullerane-C20-Ih
|
|||
| Identifiers | |||
|
3D model (Jmol)
|
|||
| ChEBI | |||
| ChemSpider | |||
|
PubChem CID
|
|||
|
|||
|
|||
| Properties | |||
| C20H20 | |||
| Molar mass | 260.38 g·mol−1 | ||
| Melting point | 430±10°C | ||
| Related compounds | |||
|
Related hydrocarbons
|
Cubane Tetrahedrane Pagodane (an isomer of dodecahedrane) Prismane |
||
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|||
 (what is   ?) |
|||
| Infobox references | |||
Dodecahedrane is a chemical compound (C20H20) first synthesised by Leo Paquette of Ohio State University in 1982, primarily for the "aesthetically pleasing symmetry of the dodecahedral framework". It is the simplest hydrocarbon with full icosahedral symmetry.
In this molecule, each vertex is a carbon atom that bonds to three neighbouring carbon atoms. The 108° angle of each regular pentagon is close to the ideal bond angle of 109.5° for an sp3 hybridised atom. Each carbon atom is bonded to a hydrogen atom as well. The molecule, like fullerene, has Ihsymmetry, evidenced by its proton NMR spectrum in which all hydrogen atoms appear at a single chemical shift of 3.38 ppm. Dodecahedrane is one of the Platonic hydrocarbons, the others being cubane and tetrahedrane, and does not occur in nature.
For over 30 years, several research groups actively pursued the total synthesis of dodecahedrane. A review article published in 1978 just dealt with the different strategies that existed up to then. The first attempt was initiated in 1964 by R.B. Woodward with the synthesis of the compound triquinacene which was thought to be able to simply dimerize to dodecahedrane. While Paquette´s group was the first to synthesize dodecahedrane, it was the Prinzbach group who found a much more versatile approach to dodecahedrane via the pagodane route (see below). Other groups were also in the race, for example that of Philip Eaton and Paul von Ragué Schleyer, yet, the task to reach the summit was reserved for the Paquette and Prinzbach teams.
...
Wikipedia