Rate of formation of N-(hydroxymethyl)benzamide derivatives in water as a function of pH and their equilibrium constants

✍ Scribed by Ramana V. Ankem; John L. Murphy; Richard W. Nagorski

• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 181 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.09.009

✦ Synopsis

The third-order rate constants for the pH-dependent formation of the carbinolamides generated from the reaction of formaldehyde and benzamide, 4-chloro, 4-nitro, 4-methyl and 4-methoxybenzamide, are reported. The acid-catalyzed reaction was found to occur via rate-limiting proton transfer, whereas the hydroxide-dependent reaction occurred via a specific-base process. Coupling the rate constants for carbinolamide formation reported herein with the previously established rates for carbinolamide breakdown yielded equilibrium constants for the carbinolamides studied in water.