Kinetic And Mechanistic Effects Of Substituents On The Aldehyde Portion Of N-(hydroxybenzyl) Benzamides

Prior research within the group on N-(hydroxybenzyl)acetamides showed an unexpected break in the Hammet plot for one of the constants of the hydroxide dependent breakdown. In order to determine the origin and structural breadth that resulted in the break in the Hammet plot, a new set a compounds have been synthesized. The N-(α-Hydroxybenzyl)benzamide derivatives were synthesized via a three part synthesis. These novel compounds were purified and fully characterized. Upon synthesis kinetic studies of the carbinolamides performed in water as a function of pH. Analysis of the data and construction of Hammet plots showed similar results to previous studies including the anomaly observed in the hydroxide dependant breakdown