[ExI] Spirited molecules

[Brent Neal]

On 4 Dec, 2009, at 14:55, Robert Bradbury wrote:

> Well, I had some difficulty reading this post as I do not read the  
> ExICh list frequently (due to its gestapo policies).
>
> But this topic attracted my attention.
>
> Thel unbonded "azide" molecule (with the formula CN4) does not exist  
> (to the best of my knowledge to assay it).  The best using Wikipedia  
> that I have been able to find is possibly N3- and therefore  
> molecules such as NaN3 (sodium azide). The statement by Derek with  
> respect to a "Cyanogen azide" suggests a C2N2 bonded to a N4  
> molecule -- which I fail to understand (I can posit plausible  
> explanations for the distribution of the electrons (around many  
> molecules) -- but I cannot posit how it is created or its actual  
> normal chemical makeup.
>
> Robert



Robert -
I think you've misunderstood the formula from the name. Cyanogen azide  
has the empirical formula CN4.  Structurally, its N≡C-N=N=N. (That's  
a triple bond between the first N and the C, in case your mailreader  
isn't Unicode savvy.) The azide functional group is delta+ on the  
middle N, and delta- on the outer N. Its just not that terribly  
stable, alas, and as Derek points out, it wants to become mostly  
nitrogen gas in the worst kind of way.

(NB: I have been known to use the sulfonyl azides to do insertions on  
polyolefins.

B

--
Brent Neal, Ph.D.
http://brentn.freeshell.org
<brentn at freeshell.org>