Kinetics of Reaction of Triethylammonium Carboxylates with α-Halogenocarbonyl Compounds in Organic Solvents. Part-II. Reaction of trans-Cinnamates with Phenacyl Bromide in Acetonel

Department of Chemistry, Bharathidasan University, Tiruchirapalli-620 024

Manuscript received 11 December 1985, revised 23 June 1986, accepted 13 November 1986

The second order rate constants (K₂) for the reaction of phenacyl bromide with triethylammonium para-substituted trans-cinuamates in acetone have been determined at 103, 303 wild 313 K and the activation parameters evaluated. The effect of addition of water on the rate constant is rationalised. Electron-releasing groups retard the reaction while electron-withdrawing groups facilitate it. The reversal of the order of the substituent effects has been rationalised. Linear regression analysis of log K₂ with Hammett σ gave a \(\rho\) value of + 0.19 with r = 0.997.