Kinetics of Analytical Acylations Catalyzed by N-substituted Imidazoles

2-methyl-N-ethylimidazole 2-picoline 2-propanol by acetic acetic anhydride acetonitrile Acetyl chloride acetylation of 2-propanol acetylation of isopropanol AcMeIm Cl ACN+ acyl acceptor Acylating Agents acylation of alcohols Aldrich alkyl group amines analytical acylation ANDREW OSAHENIN OBASEKI anhydride after hydrolysis anhydride at 45°C catalyze acylations CATALYZED BY N-SUBSTITUTED catalyzed by NMIM chloric acid chloride Connors and Pandit d[ACOR determinations DMAP dride entropy of activation ester ethanol FIGURE Gas chromatographic hydroxy hydroxy compound imidazole ring Initial concentrations intermediate isopropanol by acetic K_1[OAc K₁[N K₂[ROH KNMIM Kobs leaving group N-acetylimidazole N-alkylimidazoles N-hexylimidazole N-methylimidazole N-pentylimidazole N-substituted imidazoles NMIM acts NMIM-catalyzed acetylation NMR spectrum nucleophilic catalyst Pandit 24 phenols phthalic anhydride Pyridine rate-determining step reactive reagent relative rate second step Second-order plot second-order rate constant shows sodium hydroxide solution solvent Spectrophotometric step r.d.s. succinic anhydride t(min Table temperature third-order rate constant tion Titration of unreacted titrimetric UNIVERSITY OF WISCONSIN-MADISON unreacted anhydride versus