Dodecahedrane

Title: Dodecahedrane
CAS Registry Number: 4493-23-6
CAS Name: Hexadecahydro-5,2,1,6,3,4-[2,3]butanediyl[1,4]diylidenedipentaleno[2,1,6-cde:2¢,1¢,6¢-gha]pentalene
Additional Names: pentagonal dodecahedrane
Molecular Formula: C20H20
Molecular Weight: 260.37
Percent Composition: C 92.26%, H 7.74%
Literature References: Classical uniform convex polyhedrane. Theoretical studies: O. Ermer, Angew. Chem. Int. Ed. 16, 411 (1977); R. L. Disch, J. M. Schulman, J. Am. Chem. Soc. 103, 3297 (1981). Review of synthetic studies: P. E. Eaton, Tetrahedron 35, 2189-2223 (1979). Total synthesis: R. J. Ternansky et al., J. Am. Chem. Soc. 104, 4503 (1982).
Properties: Crystals from benzene, mp >450°.
Melting point: mp >450°
Dodecamethylcyclohexasiloxane Dodecamethylpentasiloxane Dodecarbonium Chloride Dodemorph Dodine

Dodecahedrane
Dodecahedrane-3D-sticks.png Dodecahedrane-3D-vdW.png
Identifiers
CAS number 4493-23-6
PubChem 123218
ChemSpider 109833 YesY
ChEBI CHEBI:33013 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C20H20
Molar mass 260.37 g mol−1
Related compounds
Related hydrocarbons Cubane
Tetrahedrane
Pagodane (an isomer of dodecahedrane)
Prismane
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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".[1][2]

In this molecule,[3] 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 Ih symmetry, 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.