[Garneck]

Hi!

I have a bad day with NMR spectra today. I offered to help my girlfriend with her spectrum analysis and now I have to help interpret one that belongs her friend.

I'm so confused on this one. All I can say is that the shift at 4.3 ppm is from an NH₂- gruop connected to a benzene ring. What those sextets are - I really have no idea. And the signal at 7.2 is a mysery to me, because it has no integral and it's neither a methoxy grop or a hydroxyl group.

This is, hopefully, the last time I'm bothering you with these spectras. Thanks in advance!

[dexangeles]

determining a compound is usually hard with H NMR alone.  Is thatall they're given for information?

[Garneck]

determining a compound is usually hard with H NMR alone.  Is thatall they're given for information?

Yeah, well that's the problem - they didn't get anything else. Besides doing a functional analysis - this is supposed to be an aromatic amine and it has a chlorine atom - they didn't get any other info.

And I'm totally stuck on those two sextets  

[Winga]

Only a spectrum?
Any other information? e.g. molecular formula

[Dude]

peak at 7.24 is likely residual chloroform from the deuterated solvent.  With the limited information, I would initially guess 4-chloroaniline since there are only two peaks (must be symmetrical).

[Garneck]

Only a spectrum?
Any other information? e.g. molecular formula

Yes sir, only a spectrum.

peak at 7.24 is likely residual chloroform from the deuterated solvent.  With the limited information, I would initially guess 4-chloroaniline since there are only two peaks (must be symmetrical).

Ok, but p-chloroaniline wouldn't give two sextets, now would it?

[Winga]

The J-coupling, ⁴J is still greater than 0 in aromatic compounds.

[movies]

I agree with Dude, looks like a p-substituted benzene ring.  The signal at ~7.2 is definitely CHCl₃ from the NMR solvent.

The additional splitting you see could possibly be from coupling of the NH protons to the ring protons.  These couplings will be very small.