Cuneane

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Cuneane
Ball and stick model of cuneane (1R,2R,3S,4S,5S,6R,7R,8S)
Identifiers
20656-23-9 YesY
ChemSpider 124127 YesY
Jmol 3D model Interactive image
PubChem 140734
54749138 2R,4R,6R,8R
11194301 2S,4S,6S,8S
  • InChI=1S/C8H8/c1-2-5(1)6-3-4(6)8(2)7(1)3/h1-8H YesY
    Key: YIJMEXRVJPVGIY-UHFFFAOYSA-N YesY
  • C12C3C4C3C5C1C2C45
Properties
C8H8
Molar mass 104.15 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).
Infobox references

Cuneane (C8H8, Pentacyclo[3.3.0.0 2,4.03,7.06,8]octane) is a saturated hydrocarbon.[1] Its name is derived from the Latin “cuneus”, meaning a wedge.[2] Cuneane may be produced from cubane by metal-ion-catalyzed σ-bond rearrangement.[3][4] Similar reactions are known for homocubane (C9H10) and bishomocubane (C10H10).[5][6]

The cuneane molecule has three groups of equivalent carbon atoms (A, B, C), which have also been confirmed by NMR.[7] 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.[8][9]

Scheme 2. Equivalent carbon atoms in cuneane

Some cuneane derivatives have liquid crystal properties.[10]

External links

  • 2D and 3D Models of Dodecahedrane and Cuneane Assemblies Link

References

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  1. with 3D-structure (however molecular graph of cuneane is a planar graph)
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