Hi, I have a question in forming ionic complex.

I see some people making ionic complex of partially ionizable drug to increase lipophilicty and incorporate it into the lipid matrix.

However, a lot of these reactions were performed in organic solution that are not polar enough to ionize molecules, such as ethanol, DMSO, DCM, or chloroform. DMSO, DCM, and Chlorofrom do not especially participate in reaction as far as I know.

For example, NH2 group in Doxorubicin base is ion complexed with COOH group in oleic acid in DMSO. From what I understand though, DMSO is not polar enough to ionize NH2 to NH3+ or COOH to COO-.

How can these molecules be charged and form ion complex in a solvent that does not have hydrogen donor or acceptor?

Second example, siRNA and hyperbranched-PEI was complexed in chloroform. However, I do not think chloroform has hydrogen donor that can charge NH2 in PEI ?

I think I am missing something important in ionization or ion complexation. Could anybody help me out what I am understanding wrong and delineate the ion complex formation based on the examples I gave you above?

Thanks