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Topic: 1H NMR Help  (Read 3498 times)

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Offline MasterMatt

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1H NMR Help
« on: October 06, 2013, 05:09:06 PM »
Hello I need some help with an 1H NMR problem. I have uploaded images of the spectra (partially assigned) and a picture of the reaction that the NMR is from, with labelled protons.

Here it is: http://imgur.com/a/mizvJ (sorry for some reason they uploaded upside down)

I am having trouble with the 1.4 to 1.8 region with the nine and 6 peaks. Starting with the nine peaks, I believe they are due to H(I) coupling with the six H(H) protons and the two H(J) protons, but i can't seem to figure out a coupling diagram that works. It almost looks like a sextet and a triplet in the same region, but that doesn't make sense.

Thanks for any help :)

Offline Archer

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Re: 1H NMR Help
« Reply #1 on: October 06, 2013, 06:10:01 PM »
The nine peaks seen here is very common for this type of substance. Essentially you use 6 and 2 so the n+1 rule suggests 9 peaks. However they are non equivalent so this cannot apply. Instead your coupling constants (J, Hz) are such that you have overlapping peaks so you have a "pseudo nonuplet" made up of a triplet of sextets which overlap. when peaks overlap the intensity increases proportionately (see doublet of doublets which overlaps to form an apparent triplet). This is, however, a multiplet and should be reported as such, it should not be reported as a nonuplet (spelling may be wrong)

Draw your Pascals triangle and work out the relative peak heights for your three sextets in excel (or similar)  and then overlap them so you get 9 peaks. The heights should match what you have.

I made a great many of these  isobutyl type compounds during my PhD, I just assumed the n+1 rule applied and accepted 9 peaks. Credit to you for questioning it, I didn't and someone made me look a fool during a presentation by asking the same question you have raised.
« Last Edit: October 06, 2013, 06:34:01 PM by Archer »
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Offline MasterMatt

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Re: 1H NMR Help
« Reply #2 on: October 06, 2013, 06:45:19 PM »
Okay thank you for your reply. Why is it a triplet of sextets and not a triplet of septets? (6 equivalent protons +1)

Offline Archer

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Re: 1H NMR Help
« Reply #3 on: October 06, 2013, 06:56:00 PM »
Okay thank you for your reply. Why is it a triplet of sextets and not a triplet of septets? (6 equivalent protons +1)

Well spotted, forgive my error it is late here in Ol' Blighty. You are quite right, it is essentially an overlapping triplet of septets!
“ I love him. He's hops. He's barley. He's protein. He's a meal. ”

Denis Leary.

Offline MasterMatt

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Re: 1H NMR Help
« Reply #4 on: October 06, 2013, 07:21:42 PM »
Great thanks! Just making sure I wan't missing something :)

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