FOOF is only stable at low temperatures; you'll never get close to RT with the stuff without it tearing itself to pieces. I've seen one reference to storing it as a solid at 90 Kelvin for later use, but that paper, a 1962 effort from A. G. Streng of Temple University, is deeply alarming in several ways. Not only did Streng prepare multiple batches of dioxygen difluoride and keep it around, he was apparently charged with finding out what it did to things. All sorts of things. One damn thing after another, actually:
"Being a high energy oxidizer, dioxygen difluoride reacted vigorously with organic compounds, even at temperatures close to its melting point. It reacted instantaneously with solid ethyl alcohol, producing a blue flame and an explosion. When a drop of liquid 02F2 was added to liquid methane, cooled at 90°K., a white flame was produced instantaneously, which turned green upon further burning. When 0.2 (mL) of liquid 02F2 was added to 0.5 (mL) of liquid CH4 at 90°K., a violent explosion occurred."
And he's just getting warmed up, if that's the right phrase to use for something that detonates things at -180C (that's -300 Fahrenheit, if you only have a kitchen thermometer). The great majority of Streng's reactions have surely never been run again. The paper goes on to react FOOF with everything else you wouldn't react it with: ammonia ("vigorous", this at 100K), water ice (explosion, natch), chlorine ("violent explosion", so he added it more slowly the second time), red phosphorus (not good), bromine fluoride, chlorine trifluoride (say what?), perchloryl fluoride (!), tetrafluorohydrazine (how on Earth. . .), and on, and on. If the paper weren't laid out in complete grammatical sentences and published in JACS, you'd swear it was the work of a violent lunatic. I ran out of vulgar expletives after the second page. A. G. Streng, folks, absolutely takes the corrosive exploding cake, and I have to tip my asbestos-lined titanium hat to him.
Good lord! Who WAS this Streng guy? He had to be a Spark or Mad of some kind!
If you work with the halogen azides, you work with things whose essential character time does not alter.
"Until they blow up", you say. Ah, but that is their essential character. It's the things around them that alter. Make sure you don't put anything next to them that you're not comfortable seeing altered - you know, all sudden-like.
Tetrazole derivatives have featured several times here in "Things I Won't Work With", which might give you the impression that they're invariably explosive. Not so - most of them are perfectly reasonable things. A tetrazole-for-carboxyl switch is one of the standard med-chem tricks, standard enough to have appeared in several marketed drugs. And that should be recommendation enough, since the FDA takes a dim view of exploding pharmaceuticals (nitroglycerine notwithstanding; that one was grandfathered in). No, tetrazoles are good citizens. Most of the time.
It's when they get put in with the wrong sort of company that they turn delinquent. What with four nitrogens in the ring and only one carbon, they do have a family history of possible trouble - several sections of this blog category could just as accurately be called Things That Suddenly Want To Turn Back Into Elemental Nitrogen. And thermodynamically, there aren't many gently sloping paths down to nitrogen gas, unfortunately. Both enthalpy and entropy tilt things pretty sharply. A molecule may be tamed because it just can't find a way down the big slide, but if it can, well, it's time to put on the armor, insert the earplugs, and get ready to watch the free energy equation do its thing right in front of your eyes. Your heavily shielded eyes, that is, if you have any sense at all.
Nitro groups are just the kind of bad company I mean, since they both bring their own oxygens to the party and pull electrons around in delightfully destabilizing ways. So nitrotetrazole is already not something I'd feel good about handling (its metal salts are primary explosives), but today's paper goes a step further and makes an N-oxide out of a nitrogen on a nitrotetrazole ring. This both adds more oxygen and tends to make the crystal packing tighter, which raises the all-important kapow/gram ratio. (There is, of course, little reason to do this unless you feel that life is empty without sudden loud noises). The paper mentions that "Introducing N-oxides onto the tetrazole ring may . . . push the limits of well-explored tetrazole chemistry into a new, unexplored, dimension.", but (of more immediate importance) it may also push pieces of your lab equipment into unexplored parts of the far wall.
I love this guy.
I just want to quote again - "The all-important kapow/gram ratio." Because somehow, some way, I'm going to steal that and use it. The line, I mean. Not the kapow. ^_^;;
Hrmmmm I was once accused of using technobabble when I was explaining how a Tesla coil worked to an audience. It haunts me still. I'd love to ask that person to better explain how I lit up a lightbulb that wasn't plugged into anything.
An early favorite has appeared in my “most alarming chemical papers” file for this year. Thomas Klapoetke and Joerg Stierstorfer from Munich have published one with a simple title that might not sound unusual to people outside the field, but has made every chemist I’ve shown it to point like a bird dog: “The CN7 Anion”. The reason that one gets our attention is that compounds with lots of nitrogens in them – more specifically, compounds with a high percentage of nitrogen by weight – are a spirited bunch. They hear the distant call of the wild, and they know that with just one leap of the fence they can fly free as molecules of nitrogen gas. And that’s never an orderly process. If my presumably distant cousin Nick Lowe does indeed love the sound of breaking glass, then these are his kinds of compounds. A more accurate song title for these latest creations would be “I Love the Sound Of Shrapnel Bouncing Off My Welder’s Mask”, but that sort of breaks up the rhythm.