Cubanes

Cubane is a synthetic hydrocarbon compound with the formula . It consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole. Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles". The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained a

Octanitrocubane (molecular formula: C8(NO2)8) is a proposed high explosive that, like TNT, is shock-insensitive (not readily detonated by shock). The octanitrocubane molecule has the same chemical structure as cubane (C8H8) except that each of the eight hydrogen atoms is replaced by a nitro group (NO2). As of 1998, octanitrocubane had not been produced in quantities large enough to test its performance as an explosive.

Heptanitrocubane is an experimental high explosive based on the cubic eight-carbon cubane molecule and closely related to octanitrocubane. Seven of the eight hydrogen atoms at the corners of the cubane molecule are replaced by nitro groups, giving the final molecular formula .

Octafluorocubane or perfluorocubane is an organofluorine compound with the formula , 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 the ester of carboxycubane, beginning with its heptafluorination. According to X-ray crystallography, the C–C distances (1.570 Å) in octafluorocubane are consistent in length with those in the parent cubane (1.572 Å).