Lotilko - 10-9-2016 at 14:58
I wasn't sure where to post this because Bert seems to be grumpy about newcomers posting new topics in the Energetics section and the questions in the
Short Questions / answer thread are sometimes ignored when there is another discussion going on. Not sure if the Beginnings is the right place for
this, but here it goes:
I was reading about high nitrogen content salts and stumbled across 5-Hydrazino-1H-tetrazolate, so I thought why not replace that hydrogen with
something else. Maybe another hydrazino group? Why not?
You see, I'm really not good with chemichal nomenclature, but I suppose it's called 1,5-Dihydrazinotetrazole, but correct me if I'm wrong.
So as I searched for an applicable preparation route, I haven't found anything about this compound, I'm not even sure of it's existence. I know that
primary amines react with aqueous hydrazine to form the corresponding hydrazine and ammonia.
My idea would be to react one equivalent 1,5-Diaminotetrazole with two equivalents of hydrazine to form 1 eq. of 1,5-Dihydrazinotetrazole and two eqs.
of ammonia.
What do you all think?
Metacelsus - 10-9-2016 at 16:39
I think that substitution reaction probably wouldn't work. Is there any precedent for it?
Lotilko - 11-9-2016 at 04:46
In Advanced Energetic Materials Based On 5-Aminotetrazole, there is a reaction scheme on page 83-84 showing the reaction of aminoguanidium perchlorate
with hydrazine to produce triaminoguanidium perchlorate and ammonia.
PHILOU Zrealone - 14-9-2016 at 04:42
Maybe you could go to hydrazinoaminotetrazole...and if it is stable, what I doubt, dihydrazinotetrazole would be nice energetic material or starting
material
I doubt it would be stable because it would imply the sequence H2N-NH-N-N-N-N- thus 6N atoms linked together...what is really a lot.
Lotilko - 20-10-2016 at 13:43
My bad, amine substitution will definitely not work for the nitrogen. The functional groups on the carbon can be greatly varied, because of the vast
array of reactions that it can undergo.
Maybe if one reacted the tetrazole with tosyl chloride or triflic anhydride in a protic solvent, one could synthetize the tosyl or triflyl derivative
and since these are excellent leaving groups, one could substitute these. Wikipedia states that the triflyl group easily undergoes nucleophilic
reactions. This reaction works for 5-Aminotetrazole with tosyl chloride in Et3N, but ring cleavage occurs because of basic media.
And regarding your predictions PHILOU, 1,5-Dinitraminotetrazole has been prepared and is stable despite the 6 nitrogens linked together. As far as I
know, nitro groups destabilize molecules so if 1,5-Dinitraminotetrazole is stable, shouldn't the 1,5-dihydrazino derivative be more stable. It's just
an idea, but if it's not the case, then please elighten me.