Superimposed general base catalysis in anilide hydrolysis

✍ Scribed by Richard L. Schowen; George W. Zuorick

• Book ID: 104240433
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 106 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89134-6

✦ Synopsis

Biechler and Taft2 showed that 2,2,2-trifluoro-N-methylacetanilide (I) hydrolyzes at a rate given by eq. 1, and attributed the term second-order in hydroxide to the intermediacy of the dinegative ion II. -d[Il/dt = [II (k,[RO-I + kz[RO-12)

(1)

We have confirmed eq. 1 and have in addition shown by studies in buffered solutions (Table I) that general base catalysis is superimposed on hydroxideion catalysis in the hydrolysis of I. The complete rate expression in basic solution is then given by eq. 2, where the surmnation is over all bases, Bi, present. Ihe values of ki for various bases are shown in Table II.