Dodecahedrane

Dodecahedrane is a chemical compound, a hydrocarbon with formula C20H20, whose carbon atoms are arranged as the vertices (corners) of a regular dodecahedron. Each carbon is bound to three neighbouring carbon atoms and to a hydrogen atom. This compound is one of the three possible Platonic hydrocarbons, the other two being cubane and tetrahedrane.

Dodecahedrane
Names
IUPAC names
(C20-Ih)[5]fullerane
hexadecahydro-1,6,5,2,4,3-(epibutane[1,1,2,3,4,4]hexayl)dipentaleno[2,1,6-gha:2′,1′,6′-cde]pentalene
Systematic IUPAC name
undecacyclo[9.9.0.02,9.03,7.04,20.05,18.06,16.08,15.010,14.012,19.013,17]icosane
Identifiers
3D model (JSmol)
1880116
ChEBI
ChemSpider
1326921
PubChem CID
UNII
  • InChI=1S/C20H20/c1-2-5-7-3(1)9-10-4(1)8-6(2)12-11(5)17-13(7)15(9)19-16(10)14(8)18(12)20(17)19/h1-20H Y
    Key: OOHPORRAEMMMCX-UHFFFAOYSA-N Y
  • InChI=1/C20H20/c1-2-5-7-3(1)9-10-4(1)8-6(2)12-11(5)17-13(7)15(9)19-16(10)14(8)18(12)20(17)19/h1-20H
    Key: OOHPORRAEMMMCX-UHFFFAOYAM
SMILES
  • C12C3C4C5C1C6C7C2C8C3C9C4C1C5C6C2C7C8C9C12
  • C31C%10C2C5C%11C6C8C(C1C9C4C7C(C2C34)C5C6C7C89)C%10%11
Properties
C20H20
Molar mass 260.380 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).
Y verify (what is YN ?)
Infobox references

Dodecahedrane does not occur in nature and has no significant uses. It was synthesized by Leo Paquette in 1982, primarily for the "aesthetically pleasing symmetry of the dodecahedral framework".

For many years, dodecahedrane was the simplest real carbon-based molecule with full icosahedral symmetry. Buckminsterfullerene (C60), discovered in 1985, also has the same symmetry, but has three times as many carbons and 50% more atoms overall. The synthesis of the C20 fullerene C20 in 2000, from brominated dodecahedrane, may have demoted C20H20 to second place.

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