Author Topic: formulae for describing kinetics of base catalyzed amide/ether hydrolysii? -rev dron  (Read 1330 times)

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Author  Topic:   formulae for describing kinetics of base catalyzed amide/ether hydrolysii? 
rev drone
Hive Bee   posted 01-21-2000 03:54 PM          
Yes, I'm being a bit lazy, but considering all the stuff I do, I'm entitled every now and then.
Just in case anybody has this information at their fingertips, does anybody know the general formula describing the base-catalyzed hydrolisis of amides or esters? For that matter, acid-catalyzed hydrolysis kinetics data is welcome too.

-the good reverend drone

Ipsa scientia potestas est

Hive Bee   posted 01-21-2000 05:49 PM          
Hoping this is helping...
March 3rd ed p226

Bronsted catalysis equation

logk = A logKa + C

where k is the rate constant for a reaction catalyzed by an acid of ionization constant Ka. So, when k is plotted against Ka for catalysis of a given reaction by a series of acids a staight line should be obtained with slope A and intercept C.

Hive Bee   posted 01-21-2000 08:39 PM          
Saponification of an ester using a base gives the salt of a carboxylic acid:
CH2O(C=O)(CH2)14CH3 --NaOH/H2O/heat-->
CH2OH + CH3(CH2)14(C=O)O-Na+

Nitriles or amides can also be hydrolyzed in base...due to the high stability of the amide function however, acidic conditions are usually used...the reaction is driven by protonation of the amine generated, forming an ammonium ion. Because acid is consumed, it is an acid-induced rather than catalyzed reaction:

Methylamine + acetate ion <--OH-/H2O--
N-methylacetamide --H3O+/H2O--> acetic acid + methylammonium ion

this the kind of info you're looking for, or more kinetics?