MadSci Network: Chemistry
Query:

Re: Nitrocubanes. Is there a way to do a project with this molecule???

Date: Thu May 27 10:27:25 1999
Posted By: Dan Berger, Faculty Chemistry/Science, Bluffton College
Area of science: Chemistry
ID: 926324962.Ch
Message:

nitrocubane Nitrocubanes. Is there a way to do a project with this molecule???

The cubic cluster hydrocarbon cubane is kinetically stable but thermodynamically highly unstable molecule. It is foreseen to be used in the manufacture of future explosives.


Dear Tanbera,

If you plan to blow up something, I suggest you find a cheaper explosive. If you plan to do an actual research project with nitrocubanes, you'd better find an advisor with a high tolerance for destruction.

Nitrocubanes have been made (check out back issues of the Journal of the American Chemical Society and Journal of Organic Chemistry), and they do pack something of a bang. Cubane itself was first synthesized in about 1964, by Philip Eaton's group at the University of Chicago, and is surprisingly easy to make for such an unlikely-looking structure. Functionalizing it is something else again, but apparently it's relatively easy to make cubanedicarboxylic acids.

cubane But "relatively easy" means less than ten synthetic steps. It's still not exactly a simple process, and requires a good synthetic hand. Apart from the danger involved with nitrocubane, cubane itself might be a good project for an advanced undergraduate chemist; check out J. Chem. Ed. 1976, 53, 477.

Incidentally, there was an interesting article published some years back (I think in J. Org. Chem.) by a computational chemist at a US Army weapons lab; the topic was whether introducing nitrogen atoms into the cage structure would introduce enough extra instability to make cubane a worthwhile explosive, while retaining enough kinetic stability to work with. I think his conclusion was that replacing two carbon atoms (diagonally opposite) with nitrogens would be the optimum solution. But the weakness of a theoretical study like this one is that it's like the recipe for rabbit stew: first, catch your rabbit...

The simplest place to find information on cubane is at the Mining Company; here's their cubane page.

  Dan Berger
  Bluffton College
  http://cs.bluffton.edu/~berger


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