Flutterby™! : More Nitrogen

Derek Lowe: What This Here Compound Needs Is Some Hydrogen Peroxide.

Take this paper from Jean’ne Shreeve’s group at Idaho, a lab that has certainly given us all some alarming compounds over the years. If you or I (’cause we’re sensible, right?) look at a well-known crater-maker like dinitropyrazolopyrazole, we’ll probably decide that it has pretty much all the nitrogens it needs, if not more. But that latest paper builds off the question “How do we cram more nitro groups into this thing?”, and that’s something that wouldn’t have occurred to me to ask. Saying “this compounds doesn’t have enough nitro groups” is, for most chemists, like saying “You know, this lab doesn’t have enough flying glass in it” – pretty much the same observation, in the end. The way to stuff in more nitros, in case you’re wondering, is to hang hemiaminals off the NH groups and then nitrate those. (Edit: or, as shown at right, make the N-amino compounds and nitrate that). Why not? Round-bottom flasks, rota-vaps, and balances aren’t supposed to last forever, right?

Best comment: tango_uniform observes that

“More Nitrogen” is to inorganic chem as “More Cowbell” is to sketch comedy.