Editing DTBP-polyAmine (section)

=== Hydrolysis  ===

'''Ester''' 

When in the presence of a nucleophile, an ester may undergo reaction leading to cleavage of the carbonyl carbon-ether bond as shown below 

[[Image:Hydrolysis of ester.jpg]] 

'''Amide''' 

Due to their electronic similarity to esters, amides can also undergo hydrolysis, but they are less susceptible to nucleophilic attack such as that involved in hydrolysis reactions, again due to resonance stabilization and the donating of nitrogen’s NBEs to the carbonyl carbon. This delocalization has the effect of reducing the electrophilicity (reduce the partial positive charge) of the carbonyl carbon, and thereby reducing its ability to undergo attack by nucleophiles such as water or hydroxide in hydrolysis reactions: 

[[Image:Hydrolysis of amides.jpg]] 

Oxygen is more electronegative than nitrogen, thus it is less&nbsp;likely to donate its NBEs to the adjacent carbonyl. As a result, there is a lower degree of resonance delocalization through the ester carbonyl than there is in the amide carbonyl. This results in ester carbonyl carbons being relatively more electron deficient, or more electrophilic, than amide carbonyl carbons. This difference in carbonyl electrophilicity accounts for the difference in reactivity between esters and amides. It is important to understand that amides do undergo hydrolysis! The difference is the "ease" or rate at which hydrolysis occurs. Amides undergo hydrolysis at a slower rate than structurally related esters under comparable reaction conditions. 

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It is important to understand that amides do undergo hydrolysis! The difference is the "ease" or rate at which hydrolysis occurs. Amides undergo hydrolysis at a slower rate than structurally related esters under comparable reaction conditions. Consider the general example below. When placed in an aqueous alcohol solvent in the presence of base, the hydrolysis of the ester shown below may be&nbsp;complete in several hours. Under the same reaction conditions, it may take days (or longer) for the structurally similar amide to hydrolyzed! 

[[Image:Amide ester hydrolysis.jpg]] 

[[Category:Transfection]] [[Category:Paul]]