OT: Organic Chemistry

[Cursitor Doom]

Gentlemen,

As we all know, whenever a question arises concerning the origins of the universe, or the synthesis of complex macromolecules, the first place we turn for answers is uk.d-i-y, where hundreds of highly qualified scientists eagerly await the chance to address such recondite matters. I now set before them this apparently insoluble conundrum.

This apparently simple molecule doesn't exist in nature and cannot be synthesised in the structure shown. Why not?

Molecular formula: C3H6N2

Structure: H-N-C=C-C=N-H | | | | H H H H

(view in proportional font). A 10 shilling postal order will be sent to the poster with the correct solution.

[The Natural Philosopher]

A cursory google indicates that its generally found in a ring structrure ergo I would asume the ring is more stable

But really I haven't done ths shit since 1968

[Fredxx]

How much do you need?

[Jeff Layman]

There is a section titled "Vendors", which suggests the chemical was available once, but the links there don't really come up with anything positive.

In any case, I would expect the chemical to be tautomeric. I came up with this (how's your German?):

Is that worth a five bob postal order?

[Martin]

The DMark 64,000 question?

[Cursitor Doom]

A not unreasonable assumption. And all the structures I've thus far seen have been annular, usually as components of 7-member heterocycles. The RSC's Chemspider site wont allow the linear conformation to be entered, though. Maybe their software's busted.

[Roger Hayter]

There's stuff called 1,2-ethylenediamine. I don't know why I've heard of it. Is the propylene 1,3 version more stable than your proposal?

It would be:

H | H-N-C-C=C-N-H | | | | | H H H H H

With a bit more hydrogen. But I've no idea.

[Dave W]

Why should I struggle to answer when you say you know it already? Why should I use a proportional font not fixed pitch? Why would I want obsolete currency? Why are you bothering this group?

[Cursitor Doom]

At the risk of pointing out the obvious, if it's a struggle for you, simply don't bother!

[Roger Hayter]

ITYDM a non-proportional, ie fixed, font, actually!

[Brian Gaff]

Probably because as Einstein said. there are limits on genius, but not on stupidity. Brian

[Dave W]

Precisely. He told us to use a proportional font.

[Roger Hayter]

It was fairly obvious that he meant the opposite, though.

[Martin Brown]

Never the less RSC Chemspider does have it in its isomers database:

Properties are only "predicted" so it seems unlikely that anyone has bothered to make it in sufficient quantity to actually measure them.

Molport shows that at least one linear isomer is stable enough to have once been sold as Acrylimidamide but not the one you specified.

H-C=C-C=N-H | | | H H N-H | H

I am slightly bemused to find that 2-diazopropane was apparently once on sale (discontinued). I wonder how they shipped it to customers?

(CH3)2C=N=N

ISTR it has a half life of 3h at 0C if it doesn't explode first.

[Cursitor Doom]

I'm no computer geek; far from it. Perhaps I should have said view it in plain text with a font such as Courier.