I have synthesized a sodium sulfate surfactant. The starting material is soluble in CDCl3 and has a nice NMR spectrum. When i try to NMR my product in CDCl3 there was zero analyte (this is important because the starting material should have shown up if it was present). When I NMR the surfactant product in d-DMSO I get what looks like a mixture of starting material and product peak shifts... could my surfactant be decomposing/reacting in DMSO? It is not soluble in anything else besides methanol and EtOAc/hexanes and pure via TLC. Thanks!
Whether it is salt ? if salt is it soluble in DMSO. DMSO may act oxidizing species.Your copmd. may be reacting with DMDO(deuterated).
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Are you are thinking along the lines of a Swern Oxidation? then you would need oxalyl chloride to react with DMSO to make Dimethylchlorosulphonium ion that could THEN oxidize alcohols, but not DMSO by itself?...
Please follow the following reference. It might be helpful
http://link.springer.com/article/10.1134/S1061933X13050037
and
http://pubs.acs.org/doi/abs/10.1021/la00029a013
Solved: I pumped on my d-DMSO for a few hours in a desiccator with NaOH pellets, dried all glassware coming into contact at 180°C, concentrated to ~75 mmol, added a single 3A MS to my NMR tube and ran the sample moments later. Complete absence of water by NMR and the peaks coalesced and out came a beautiful spectrum (SM was hepadecanoic acid reduced to alcohol then sulfonic acid then the salt). I still find it odd that water could be the culprit and almost want to chalk it up to contamination, but my previous sample had sat about 24 h in wet dmso prior to nmr... thanks for your input!!
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