Intramolecular participation of the amide group in the hydrolysis of p-nitrophenyl N-(bromoacetyl) anthranilate

Add time:07/26/2019    Source:sciencedirect.com

The rate of hydrolysis of p-nitrophenyl N-(bromoacetyl) anthranilate (Ib) has been measured in aqueous solution between pH 1 and 6.5 has been found to increase linearly with pH at pH higher than 3. An abnormally large apparent alkaline rate constant of 3.8 × 106 M−1 sec−1 has been determined. Intramolecular nucleophilic displacement by the amide group at the carbonyl carbon of the ester occurred and a cyclic intermediate was formed. This intermediate has been detected by direct isolation and by measurements of the proton release accompanying the reaction. The rates of hydrolysis of analogous derivatives (IIb-IIIb-IV), for which this intramolecular assistance was not possible, were slower by a factor of about 5 × 105. Such an example of intramolecular catalysis may be useful for a better understanding of the enzymatic catalysis.

We also recommend Trading Suppliers and Manufacturers of 4-NITROPHENYL ANTHRANILATE (cas 19176-60-4). Pls Click Website Link as below: cas 19176-60-4 suppliers

Prev:Specific influence of salts on the hydrolysis reaction rate of p-nitrophenyl anthranilate in binary acetonitrile–water solvents
Next:Antidepressant-like activity of a new piperazine derivative of xanthone in the forced swim test in mice: The involvement of serotonergic system)