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Author: Subject: Nitronate Salts & Enolates: Do they take on the solubility of the base, or maintain their own solubility?
Electra
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[*] posted on 9-5-2014 at 07:47
Nitronate Salts & Enolates: Do they take on the solubility of the base, or maintain their own solubility?


Or any full deprotonations for that matter. How is the solubility of the resulting salt determined? Often the base is water soluble and the organic compound is not, or is only partially. Is there a rule by which the solubility of these resulting enolates could be determined?

This struck me as curious when debating the use of a nitronate salt of sodium hydroxide in a grignard reaction. Perhaps it could work if the nitronate salt were made in THF or Toluene? Nitroalkanes, and Toluene, both usually being hydrophobic.

[Edited on 9-5-2014 by Electra]
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[*] posted on 9-5-2014 at 08:33


It will have its own solubility. Because they are ionic, they will tend to be less soluble in nonpolar solvents than the neutral organic molecules.



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