[Messi]

For the spectrum below, I find it weird that I get a couple of signals in the 5-6 region! No idea what those would be... If my thioamide did enolize, my hydrozen adajcent to carbon-sulfide group should only be at ~4.85ppm!

[Messi]

How do I know this? Well I did work with thioketones years ago, and saw the effects in that they like to exist as the thio enol form. I know you have an amide on the other side, but I think the thio ketone is maybe more relevant in the structure. Just my opinion, I may be wrong.
Perhaps someone else will comment on this.

I find it interesting that they are likely to exist in the thio enol form. I mentioned this to my supervisor and he disagreed with me! He said that my thio amide should rarely exist in a thio enol form.

Is this true? Why do thioketones tend to exist in the thio enol form? What is the reasoning?

[discodermolide]

I'm not sure. It may be because the d orbitals of S are low enough so the there is some overlap with the pi electrons of the enol C=C resulting in more stability.
Now this may be rubbish, if someone else can explain please do so.

[orgopete]

I don't see anything that convinces me that I am looking at a pure product, let alone anything resembling the purported product. Tell us what was done and what steps were used to isolated and purify the relation mixture.

[Messi]

I don't see anything that convinces me that I am looking at a pure product, let alone anything resembling the purported product. Tell us what was done and what steps were used to isolated and purify the relation mixture.

Hey orgo, I am in the midst of taking a C13 NMR, I'll let you know how it goes. I think I have the correct product. I'll post the NMR once I get it!

[OC pro]

Additional mass spec data as I suggested would be more convincing!

[Messi]

So, I got a 13C NMR of two of my products. The other product is currently being analyzed by the NMR machine.

Interestingly enough, my first spectra below was left overnight... but produced a worst spectra then the second one... My second one was only left in the NMR machine for about 2 hours...

Find my spectras below... looks like my desired product was formed!?