As our paper has been accepted and it will be published soon, we decided to run a small chemistry competition. We tried to synthesize a substituted azobenzene using a literature procedure….. Naturally we didn’t got the desired azobenzene but something else…. This something else have been unknown for quite a long time before we discover what it was. Will you able to unveil the unknown molecule???
Goal: guess the unknown molecule and send an email to kimikus@gmail.com with the drawn molecule and the hypothetical mechanism.
Prize: The first three that will guess the final molecule will win….. well, i don’t know what, most probably will be something 3D printed, but could be also traditional dutch food (Stroopwafels or pepernoten), or anything else… I really have no clue so far. Anyway, I’ll send the gift (if someone managed to get the right molecule) in January after I come back from vacation.
Time: the competition will be on until there will be three winners and/or the paper will be published (but so far we didn’t get any proof yet, so it will take some time).
Ground rules: People that already know the answer (group members, colleagues, friends and so on) naturally, cannot partecipate. Come on guys, i can always offer you a stroopwafel….
Good, let’s start then:
Desired reaction on the right, we didn’t manage to get even 1% of it. But we got 30-40% of the unknown product on the left. Reaction condition on the bottom.
Funnily enough the mass is the same of the desired product. But the UV-Vis is clearly not the one of an azobenzene….
1H-NMR in benzene-d6
1H-NMR in CDCl3…. did you notice something different?
13C-NMR in benzene d6
COSY NMR
HSQC NMR
HMBC NMR
So, did you guess which molecule we synthesized?