Kinetics and mechanism of large rate enhancement in an acidic aqueous cleavage of the tertiary amide bond of N-(2-methoxyphenyl)-N'-morpholinophthalamide (1)

Yoke-Leng Sim; Azhar Ariffin; M Niyaz Khan

doi:10.1016/j.bioorg.2008.03.003

Kinetics and mechanism of large rate enhancement in an acidic aqueous cleavage of the tertiary amide bond of N-(2-methoxyphenyl)-N'-morpholinophthalamide (1)

Bioorg Chem. 2008 Aug;36(4):178-82. doi: 10.1016/j.bioorg.2008.03.003. Epub 2008 Apr 25.

Authors

Yoke-Leng Sim¹, Azhar Ariffin, M Niyaz Khan

Affiliation

¹ Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.

PMID: 18440044
DOI: 10.1016/j.bioorg.2008.03.003

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acids / chemistry*
Hydrogen-Ion Concentration
Kinetics
Molecular Structure
Morpholines / chemical synthesis
Morpholines / chemistry*
Phthalic Acids / chemical synthesis
Phthalic Acids / chemistry*
Temperature

Substances

Acids
Morpholines
N'-morpholino-N-(2'-methoxyphenyl)phthalamide
Phthalic Acids