[vaselopita]

Hey all, I'm trying to use these NMRs to confirm that a powder I was given is the below compound.



HNMR http://i.imgur.com/3kwVFGQ.png
CNMR http://i.imgur.com/0JVy6qy.png
COSY http://i.imgur.com/suea5CN.png
APT http://i.imgur.com/SkYFJLq.png

Okay, so, from the HNMR (going up field) I can easily see the signal that corresponds to the Nitrogen's H, the aromatic ring, the CH2 group, and finally 2 methyls. So I think I have that under control. It also tells me there are 13 hydrogens.

The CNMR I can see the C's that correspond to the ring. It also confirms there are 11 carbons. Can't get much else from this 

The APT I can see that two of the C's from the ring don't have any H's on them, and that 4 of them do have one H each. One long peak towards the right represents that CH2 group. I'm assuming two negative peaks to the left are from the carbonyl groups?

One of my biggest concerns is how to decide that the compound is Ortho. Is there any way to determine that? Any help would be greatly appreciated, Thank you guys!


edit- last piece of data I have is the MS (191 molec. weight, confirms) and melting point (105, confirmed by what I measured)

[Archer]

Look at the splitting patterns in the aromatic region of the proton NMR. It's definitely not para as this gives a very distinctive pair of doublets, each integrating for two protons due to being equivalent either side of the ring.

Draw the ortho and meta substitutions and predict the splitting of each proton then see if either matches what you have.

[trinitrotoluene]

Maybe you can find some overtone bands via IR?

/edit   Coupling constants will also help