Kinetic and mechanistic aspects of oxidation of N-Phenyl acetamides by N-bromophthalimide in presence of excess of mercuric acetate

ORGN 114

Pabba Srinivas, sripabba85@yahoo.co.in, Department of Chemistry, Osmania University, Basheerbagh, Hyderabad, India and Amena Anjum, aanjum@chem.utoronto.ca, Department of Chemistry, University of Toronto, 292 finch Avenue West #305, Toronto, ON M2R 1N1, Canada.
Recently N-Bromoimides particularly N-bromophthalimides (NBP) have proven to be efficient and mild oxidizing agents. The oxidative kinetics of N-phenyl acetamides (PhNHAc) viz.,3-nitro,4-chloro,4-methyl,4-nitro acetanilides has been carried out by NBP in presence of excess of mercuric acetate in aqueous acetic acid medium. Results of detailed kinetic effects viz., Solvent, temperature, concentration and salt effects support the Michaelis Menten type of mechanism. The stoichiometric ratio of NBP: PhNHAc was 2:1.The product study by HPLC showed p-benzoquoines as the products of oxidation.. Thermodynamic and activation parameters have been presented and these reveal the reaction to be enthalpy controlled.