Kinetics and mechanism of large rate enhancement in an acidic aqueous cleavage of the tertiary amide bond of N-(2-methoxyphenyl)-N'-morpholinophthalamide (1).
The rate of conversion of 1 to N-(2-methoxyphenyl)phthalimide (2) within [HCl] range 5.0x10(-3)-1.0 M at 1.0M ionic strength (by NaCl) reveals the presence of both uncatalyzed and specific acid-catalyzed kinetic terms in the rate law. Intramolecular carboxamide group-assisted cleavage of amide bond of 1 reveals rate enhancement of much larger than 10(6)-fold compared to the expected rate of analogous intermolecular reaction.
Sim
Yoke-Leng
YL
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.
Ariffin
Azhar
A
Khan
M Niyaz
MN
D000143:Acids / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D010795:Phthalic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013696:Temperature
D000143:Acids; D009025:Morpholines; C530609:N'-morpholino-N-(2'-methoxyphenyl)phthalamide; D010795:Phthalic Acids