[uglepik]

If you take an organic salt (my current example is a DIPEA salt of a large lipid molecule, containing a carboxylic acid) and dissolve in an organic solvent, such as chloroform, will the dissolved species be two separate ion, surrounded by chloroform molecules (such as occurs in an aqueous solution of a salt) or will the ions be associated with each other in solution, as an ion-pair.

And furthermore... In an NMR spectrum (in CDCl3) will the ions influence each others spectra? For example would the protonated DIPEA-species have a different spectrum if the anion was different? Or would it always be the same?

Thanks for your help.

[the.khemist.ds]

In salts the counter-ion definitely affects the chemical shift. The extent of association in the ion-pair will affect the electron density on certain features - and hence the shielding effect.

It's somewhat of an extreme example, but ionic liquids are illustrative of this. The salt metathesis going from Bmim Br to Bmim BF4 has a significant effect on the chemical shift of the imidazolium protons.

I'd point out that changing the deuterated solvent that you use to perform your NMR experiment affects the spectrum.