Things I Won't Work With: Chlorine Azide | Hacker News Reader

Things I Won't Work With: Chlorine Azide

pipeline.corante.com

92 pointsjoe_bleau21 comments

The whole "things I won't work with" category is a good read: http://pipeline.corante.com/archives/things_i_wont_work_with...

along with the related category, "how not to do it": http://pipeline.corante.com/archives/how_not_to_do_it/

It remains, with its chemical relatives, off in a part of chemical science that's safe from human exploitation.

Although Sodium Azide is used in systems which save thousands of lives every year - car airbags.

http://en.wikipedia.org/wiki/Sodium_azide

Older ones, yes. Newer ones use nitroguanidine and other less-toxic stuff according to the article you linked to.

That said, we owe a lot to the brave chemists who manage to figure out how to deal with all these scary chemicals. Even if some of them are probably insane:

http://pipeline.corante.com/archives/2010/02/23/things_i_won...

I love how the chemical can be written as FOOF, which is strangely reminiscent of the bogus F00F C7C8 instruction that could crash old Pentiums.

> I love how the chemical can be written as FOOF, which is strangely reminiscent of the bogus F00F C7C8 instruction that could crash old Pentiums.

Or the sound a small explosion might make, which is the first thing most people would think of. ;-)

"it usually detonates violently whatever the temperature, without apparent provocation." -- http://en.wikipedia.org/wiki/Chlorine_azide

Anything described like that I would stay far away from too.

A drawing of the molecule (ClN3): http://chemeo.com/cid/31-110-4 just looking at it, you think, ouch! Insane high level of bounds tension coupled with a Cl detonator.

Well, bond tension by itself is not the indicator of explosiveness, isn't it? The N2 molecule has 3 bonds connecting 2 atoms and it is one of the most stable known molecules.

A triple-bond is not inherently unstable. In chlorine azide, though, you've got a strongly electronegative halide (chlorine) bound via tenuous single-bond to a partial triple-bond in the nitrogen compound. One of those nitrogens has a partial charge at all times.

Bottom line: that chlorine wants to dissociate, badly. When it does, it's going to take the azide with it. It's like a chemical hair-trigger, waiting to be pulled by the nearest partial charge.

Maybe Loic meant: "Insane high level of _potential_ bound tension coupled with a Cl detonator." (My emphasis.)

It seems to me that the Cl atom is easily removed from the N-C bond, by something as simple as water vapor. My chemistry isn't great, but I would hazard a guess that even the slight polarity of the water molecule is enough to remove the Cl from the N-C bond, thereby the potential for explosive behavior.

Info from the Wikipedia indicates as much: http://en.wikipedia.org/wiki/Chlorine_azide

Yeah, those nitrogens are seriously pissed off.

Don't anthropomorphise nitrogen. It does not like that.

You've inspired me to learn more chemistry.

I did go back to university recently and among other things I did do one term of basic chemistry. Initially it is like applied maths with weird rules, and then a lot of lab work, which is completely different. I had to work quite hard at it.

The physical chemistry part, which really was more physics than chemistry, was a lot easier for me, as it was actually logical and I could puzzle out an answer if I needed to. Whereas IMHO in a lot of chemistry, when you are new, you need to know all the exceptions by hearth.

I studied some organic chemistry and biochemistry during the IT death. I got ill, or I might be a chemist today. Really hard work, but fascinating.

I went there with the vision of building subroutine libraries and making bacteria programmable.

But biochemistry wasn't so fun, since the big proteins and other macro molecules are magical. You can't design them -- you have to get already created ones or evolve them.

Say it yourself a few times: "I love software"

Previous submissions:

http://news.ycombinator.com/item?id=1148425 (with discussion)

http://news.ycombinator.com/item?id=1560128

Those aren't previous submissions of this entry, but of (in one case) an earlier "Thing I won't work with" and (in the other) the series as a whole, which didn't then include this one.

I love this series of blog posts, especially since I have studied a bit of organic chemistry and loved that lab work (a very one-sided love affair).

As an old "fan" of rocket fuels in general and peroxides in particular, I still giggle a bit nervously at the chemical formula FOOF...

Edit: http://pipeline.corante.com/archives/2010/02/23/things_i_won... "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."

Read the comments in the linked article. You'll enjoy it.

I did, when I read it originally a year ago, or so. They are often as good as the blog post.

Sometimes I forget that there's entire armies of geeks that do crazy complex things other than compyooterz.

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