I face the problem with the stability to hydrolysis between ester and imine.
As far as I know, imine is prone to hydrolysis in acid whereas ester is in both acid and base.
My product has both imine and ester in it, but I want to selectively cleave imine. If imine I use is unstable like a typical imine, I can figure out how to remove only imine, maybe by putting a lot of water to accelerate the backward reaction, but imine of my product is kind of stable, ~N=C-Ph.
I'm digging in pKa value, which is a numerical value for how acidic or basic a chemical is, whose big difference means how much a reaction between two chemicals take place.
However, even though I compare the hydrolysis diagrams of ester and imine, I still cannot figure out how to selectively remove only one.
Do you have any idea about selective cleavage?
Are there other factors for the stability to hydrolysis except for pKa value?
Thanks.
Imines are the nitrogen containing cousins of aldehydes and ketones , thers is 5 - step for the formation of an ester from a carboxylic acid , the hydrolysis of an ester, and the differences in the rate of ester and amide hydrolysis lies the structural difference these two functional groups. For more information consult https://www.pharmaceutical - journal.com
Just an idea: If your compound is soluble in the same alcohol that has been used in esterifcation you could use that alcohol as solvent and add just enough water to hydrolyze the imine in acidic conditions.
https://pdfs.semanticscholar.org/af01/e6e86c2517399b1a18171768fcaa41b2c83d.pd
@Sylvester Peter Antai yes for sure, structural effects make difference but more detail the better.
@ K K Arora I think pKa value also includes steric hindrance.
@Jukka Salminen Thank you great idea when I do the esterification. My case is I didn't do esterification I use PMMA which includes ester in it with imine-including chemicals. But, I like your idea. Thanks
@T. H. Al-Noor what's the relation between your links and my question? I tried to figure it out, but let me ask you that.
I appreciate all of you. :)
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