Hexanitrohexaazaisowurtzitane, at first glance

Derek Lowe writes (in In the Pipeline) about the ungracefully-named hexanitrohexaazaisowurtzitane:

Let’s start with the name. Quite a mouthful, isn’t it? Believe me, that one’s pretty chewy even for experienced organic chemists. We see lots of more complicated nomenclature, of course, but this one some features some speed bumps, that make you go back to make sure that you’re reading it correctly. I’ll take you through my own thoughts as an example.

You skip to the end in chemical names – Mark Twain would have felt about them the same way he felt about the German language. But this brings me up short, because very few chemists could walk up to the board and draw an isowurtzitane. And I am not among their number. I have a vague picture of these “wurtz” compounds being funky three-dimensional cage structures, and that much only from having probably read too many photochemistry papers over the years. So the only thing that “isowurtzitane” calls to mind is some complicated framework of fused rings, looking like one of those wire sculptures that unexpectedly fold up flat when you pull on them.

Moving on out, as you do in a systematic name, I see that this is a hexaaza variation, which makes the picture a bit fuzzier. That’s a lot of nitrogens substituted for carbons, and the first thought is that this must be some weirdo condensation product of ammonia, some aldehyde, and who knows what. You can get some pretty funny-looking structures that way, like hexamethylenetetramine (which I’ve actually used a couple of times). I don’t know where those nitrogens are, I think to myself, but I’ll bet that’s how they got there, because any other pattern would be a synthetic nightmare. So far, so good. But now comes the unexpected habanero.

Hexanitro? Say what? I’d call for all the chemists who’ve ever worked with a hexanitro compound to raise their hands, but that might be assuming too much about the limb-to-chemist ratio. Nitro groups, as even people who’ve never taken a chemistry class know, can lead to firey booms, and putting six of them on one molecule can onlylead to such….

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