Kinetic Study on the Morpholinolysis of Esters Analogues to Flutamide in MeOH-H2O Mixtures: Effect of Medium on Reactivity & Mechanism


  •  Nada. Youssef    
  •  Shawky Elshazly    
  •  Ezzat. A. Hamed    

Abstract

The kinetics of the reaction of esters analogous to flutamide namely substituted phenyl acetate, butyrate and isobutryrate with morpholine in different percentages of MeOH-H2O solvent mixture are measured spectrophotometrically at 25oC. The second order rate constants increased with increasing water content. The correlation between rate constants, single, dual and multiparameters of MeOH-H2O mixed solvents namely solvatochromic parameters ?, ?, ?*, as well as correlation with solvent properties such as ?H2O, ?MeOH, [H2O]. log[H2O], and 1/? are examined. Single-parameter correlations of log kA versus ?*, and ?-parameters give good and acceptable results respectively. However, ?-parameter shows different behaviours. Addition of a second and a third parameter improved the correlation. The coefficient values of these parameters show that the titled reactions depend mainly on the non-specific solvation and minor specific solvation of the mixed solvent. The media effect can be described by means of the solvatochromic parameters of the mixed solvent.

 



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