[insertwittyname]

 I prepared this compound in the lab by a reaction between and . I then took the ¹H-NMR in CDCl₃. While I've managed to find the peaks corresponding to the various protons, I can't see the one for the proton on N in the amide group. Mestrenova predicts the missing peak at a δ value of 8.84, but the only unidentified peak I have (which might be proton I'm looking for since all other peaks have been assigned) is at a δ=5.23
However on integrating the protons, it only shows 0.15 protons, which makes me doubt if it really is the amide peak. Would be glad to hear any suggestions.
PS: I used triethylamine to neutralise the HCl formed. Could the basic nature of the amine abstract the amide proton, thus returning a value much less than expected?

[Flatbutterfly]

N has a nuclear spin I = 1 and this results in quadrupolar broadening often into the baseline.

[wildfyr]

I agree with butterfly, amide proton peaks can be broad or missing depending on exact conditions

[insertwittyname]

Flatbutterfly and wildfyr, thank you both for your help

[kriggy]

You might try to measure it in different solvent or add little bit of acid

[Flatbutterfly]

It is counter-intuitive but quadrupolar broadening increases at lower temperatures and hence running the spectrum at low T may bring the broadening into the fast NMR timescale domain and result in a sharper singlet. Hence run the spectrum at -90°C in CD2Cl2.

[clarkstill]

Try passing your CDCl3 over anhydrous basic alumina before dissolving your sample. Often amide broadening is due to hydrogen bonding with water and/or the presence of HCl (or DCl) in old bottles of chloroform.