Cuneane

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Cuneane
Ball and stick model of cuneane (1R,2R,3S,4S,5S,6R,7R,8S)
Names
Preferred IUPAC name
Pentacyclo[3.3.0.02,4.03,7.06,8]octane
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/C8H8/c1-2-5(1)6-3-4(6)8(2)7(1)3/h1-8H checkY
    Key: YIJMEXRVJPVGIY-UHFFFAOYSA-N checkY
  • C12C3C4C3C5C1C2C45
Properties
C8H8
Molar mass 104.152 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).

Cuneane (from

metal-ion-catalyzed σ-bond rearrangement.[2][3] Similar reactions are known for homocubane (C9H10) and bishomocubane (C10H12).[4][5]

Synthesis of cuneane from cubane

Molecular geometry

The carbon atoms in the cuneane molecule form a hexahedron with point group C2v. The cuneane molecule has three groups of equivalent carbon atoms (A, B, C), which have also been confirmed by

NMR.[6] 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.[7][8]

Equivalent carbon atoms in cuneane

Derivatives

Some cuneane derivatives have liquid crystal properties.[9]

References

  1. doi:10.1002/anie.196805371
    .
  2. ISBN 0-471-58589-0
    .
  3. doi:10.1021/ja00724a061
    .
  4. doi:10.1021/ja00711a082
    .
  5. doi:10.1016/S0040-4039(01)97830-X
    .
  6. doi:10.1002/cber.19731061217
    .
  7. S2CID 95809728
    .
  8. S2CID 98716956
    .
  9. S2CID 97269476
    .
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