Hello!
I am planning to get an alkoxide which should be potentially soluble in CH2Cl2.
Do you think it is okay to use CD2Cl2 to get an NMR spectrum of the alkoxide?
I am wondering if RO- anion can withdraw deuterium atoms of this solvent.
E.g. DMSO reacts with alkoxides to give dimsyl anion. And in the spectrum of sodium alkoxide in DMSO-d6 I saw signals I couldn't explan. The resulting solution of sodium alkoxide in DMSO-d6 was yellow.
I don't wanna use THF-d8 because of potential signal overlap.
Yes it's sometimes amazing how labile hydrogen atoms can be. I think if you do the spectrum quickly after making up the solution it should be good. Once any deuterium replacement takes place not only are you going to have coupling to D (spin 1), but you will get isotope shifts. That said the Ds in CD2Cl2 do not easily move. You've just got to try it and see.
I've even had a deuterium labeled compound have the Ds move all over the molecule *in the solid state*.
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