Tag Archives: organic chemistry

Molecule of the Day #1: Cubane

It’s a cube!


It’s not very good for the longevity of the┬ásingle bonds on my molecular model kit, but I did my best to get a semi-decent picture of it:


It has the formula C8H8 and it’s the second simplest prismane (polyhedral hydrocarbons with regular polygonal faces) after prismane itself:


But it’s boring and looks like a tent so I went with cubane. It was first synthesized in the 60s, but I can’t find any sort of information about its reactivity, besides a really long series of reactions to synthesize it, starting from 2-pentenone.

Cubane belongs to a family of Platonic hydrocarbons, none of which are found in nature due to angle strain, but all of which are nice to look at. Out of the five Platonic solids, only two have been synthesized in hydrocarbon form: cubane and dodecahedrane. Tetrahedrane and octahedrane could hypothetically exist, but have not yet been synthesized due to the extreme angle strain involved.

There’s also octaazacubane, which is eight nitrogen atoms bonded in a cube, with the formula N8:


which, apparently, has five times the energy density of TNT, despite being a rather stable molecule. It has a cool name, as well, but as far as nomenclature goes it falls short of this one:

Basketane, also synthesized in the 60s. It’s a basket. Two minutes of Google searching found nothing about it, so I’ll assume that not much has been done with it besides synthesizing it, and it’s as good a place as any to end this post.