Octafluorocubane

Octafluorocubane
Names
IUPAC name
1,2,3,4,5,6,7,8-octafluorocubane
Other names
perfluorocubane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C8F8/c9-1-2(10)5(13)3(1,11)7(15)4(1,12)6(2,14)8(5,7)16
    Key: DLEOOIAXKVODBG-UHFFFAOYSA-N
  • C12(C3(C4(C1(C5(C2(C3(C45F)F)F)F)F)F)F)F
Properties
C8F8
Molar mass 248.075 g·mol−1
Appearance colorless, sublimable
Density 2.429 g/cm3
Melting point 160.1–171.1 °C (320.2–340.0 °F; 433.2–444.2 K)
Related compounds
Related compounds
Octanitrocubane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Octafluorocubane or perfluorocubane is an organofluorine compound with the formula C8F8, consisting of eight carbon atoms joined into a cube, with a fluorine bonded to each carbon corner. It is a colorless, sublimable solid at room temperature. It has been of longstanding theoretical interest, but was not synthesised until 2022, when it was prepared in several steps from a cubane carboxylic ester beginning with its heptafluorination. According to X-ray crystallography, the C-C distances (1.570 Å) in octafluorocubane are identical in length to those in the parent cubane (1.572 Å).

Octafluorocubane has attracted interest from theorists because of its unusual electronic structure, which is indicated by its susceptibility to undergo reduction to a detectable anion C
8
F
8
, with the free electron trapped inside of the cube.

The compound was voted "favorite molecule of 2022" by readers of Chemical & Engineering News.