Proposal: Perdifluoroaminohexamine

[A.Q. Square]

As a portable fuel hexamine (1,3,5,7-Tetraazatricyclo[3.3.1.1^(3,7)]decane) is widely available. If its 12 hydrogens were replaced with difluoroamino (NF2) groups, the result could be a spectacularly powerful explosive. The "oxygen" balance would be perfect (C6N16F24 -> 6[CF4] + 8[N2]). Converting 24 N-F and 24 C-N bonds to 24 C-F and 8 N≡N bonds would release roughly 5064 kJ per mol of C6N16F24 (6.733 kJ/g). Having 24 fluorine atoms on the surface of one molecule might seem questionable, but the NF2 groups can arrange themselves with perfect symmetry to give every fluorine atom a place; they correspond to the 24 verticies of a truncated octahedron. The truncated octahedron can fill space without any gaps, suggesting a very dense crystal lattice for this molecule. I speculate that the fluorine shell may protect the core of the molecule from chemical action (more icing on a seemingly flawless cake):D. If you can think of a process to make this, please let me know.

[A.Q. Square]

A picture is worth 1000 words, so I uploaded one showing a model of perdifluoroaminohexamine with adjacent fluorines connected to show the truncated octahedral geometry.

An illustration of the perfect packing of truncated octahedra can be found at (http://en.wikipedia.org/wiki/Image:Bitruncated_cubic_honeycomb.png).

[megalomania]

Can you synthesize this, or are there any journals showing this material has been synthesized and is being used as an explosive or energetic fuel? Otherwise this is useless speculation and theorizing. The Forum only deals with things that actually exist, not ivory tower fantasies.

There are millions of "what if" chemicals, "potential" energetics, and exotic curiosities that have energetic properties. Rogue Science deals with what we can make now, with what we can build now, with what we can improvise, and with what oridinary people can accomplish without needing a million dollar budget at Los Alamos. Take a week off and read the rules about being a Mr. Wizard.

[A.Q. Square]

Mega, I apologize if this thread was too speculative. I posted because I think perdifluoroaminohexamine can be synthesized through processes within reach of some Forum members. I cannot confirm this because I invented the structure myself, and currently lack the resources to attempt the following schemes for synthesis. I do not demand that anyone attempt them, but I expect that success would be very rewarding.

Scheme 1: H12(hexamine) + 12[N-bromosuccinimide] -> Br12(hexamine) + 12[succinimide],
Br12(hexamine) + 12[HNF2] -> (F2N)12(hexamine) + 12[HBr]

Rationale: Bromide is a good leaving group, so brominating hexamine facilitates substitution by HNF2.

Scheme 2: H12(hexamine) + 12[NF3] + ((CH3)2CH)2NLi as catalyst -> (F2N)12(hexamine) + 12[HF]

Rationale: LDA deprotonates hexamine, and the H+ reacts with NF3 to form HF and NF2+. As NF2+ cannot react with the non-nucleophilic LDA, it joins with the deprotonated hexamine to form the product.

The first approach was suggested by my professor, and I think it the most likely to succeed. The second approach is my own, and would have the advantages of using NF3 instead of the more expensive HNF2, and expending two reagents rather than three, though the catalyst lithium diisopropylamide is expensive.

===

If I was you (unless I was planning to perform a synthesis and post the proof here, which you're not)... I'd quit while I was still a member of the forum under my current username. - Enkidu

[Charles Owlen Picket]

A.Q. Square: You may not be getting the picture, therefore I will be very succinct.
The Mr. Wizard speculative chemistry is not particularly rewarding to read nor is it practical in the context of this forum.(Strike One) A six line blurb that makes an attempt at theoretical chemistry is not particularly professional in that context either.(Strike Two)
What's more you have been told this before.

You don't have to prove your intellect to anyone. In this world no matter how well endowed you are intellectually there is always someone with a much bigger, longer, more erect intellect. Attempting to show off your grasp of theoretic chemistry may even have a bit of a bearing on the subject matter if there was some practical or utilitarian use for what you are discussing. In this case we don't have any of that.

The whole post is completely impractical and simply serves as a showcase for the bandying about of verbiage relating to theoretical chemistry. The analogy of the penis size contest is very close to the truth here. What people are seeing from all this is someone who is attempting to display "their size" intellectually, with no end-game other than ego gratification. No matter what your sexual proclivity, both girls & boys like it when you USE IT not just display it..... This is very important advice & I would think about it before you even attempt to reply.

[megalomania]

Even if the reaction does work, you left out a lot. What kinds of yields do you expect, 1%, 50%, 80%? What temperature would this reaction be run, -78C, room temp, elevated temps? How long should the reaction be run, 30 minutes, 24 hours, 3 days? Will it require an inert atmosphere, dry atmosphere, anhydrous reagents? What mole scale would this reaction work, 1-5 mmol? How can you isolate and purify the product, distillation, flash column, extraction? What byproducts will be produced? How will you characterize your product to know you have fluorine in your product if you can't run fluorine spectroscopy? Do people with access to an NMR even have probes for that on their machine? Will IR, GC, or mass spec be enough? Would you even know how to interpret a NMR spectra with all the signal splitting that many fluorines would cause?

Do you even know anything about fluorine chemistry, or are you substituting one chemical for another based on previously published reactions?

NF2 groups, which I personally like to call niflo groups until a better name comes around, has the potential to make every compound a more powerful explosive by substituting nitro for niflo.

Don't think this compound is yours just because you drew a nice picture! Better men than you have already proposed this. What matters is if you can synthesize the compound or not.

It is very irresponsible and DANGEROUS to suggest to amateur chemists that can make some untried substance with unknown properties when even professional chemists would be hesitant to tread. You are a fucking idiot if you think your reaction scheme and "perfect" oxygen balance amounts to a hill of beans. I see a lot of should, could, would in your posts. You sound like a Monday morning quarterback offering advise on something you can't do anything about.

[Jome skanish]

Is there even one known -NF2 explosive?

[Barnacles]

This type of post isnt necessarily what you are looking for, but this is too weird to leave out. Around february 20th I had a dream that I invented/discovered a new explosive and it was called perdifluoroaminonitrohexamethylene. like wtf. I am not making this up. I actually woke up and wrote it down as I do some of my more exciting or weird dreams. And I read this post when it first came out, but I just found that paper last night and had to post this.

I just found this way to crazy of a coincidence to not post this. Sorry for the semi useless post. I am not exactly captain chemistry, but I am curious if what I said is chemically possible,not whether it has actually been done, but is the molecule possible? Thanks in advance. I hope that myself and this post do not get deleted.

[megalomania]

There are dozens of difluoroamino (NF2) compounds currently in the literature. I have been collecting references for them by trolling through Chemical Abstracts structure database for compounds tagged as explosive.

There are not, to my knowledge, any commercially manufactured explosives using niflo groups yet. All are still in the experimental stages, and that could last decades. Potentially and explosive with a nitro group could be substituted with a niflo group. Nobody gets to "invent" these molecules because of this simple substitution, what you get to invent is a method of synthesis.

Even after a nitro to niflo substitution is made there is no guarantee the explosive properties will be superior, or even similar. There is a strong probability, but not a certainty. Just because something is explosive does not mean it is commercially viable. Almost all explosives are dangerously unstable, it is the 1 out of 1000 rarity like TNT and RDX that find commercial use.