Rapid amidic hydrolysis: a competitive reaction pathway under basic conditions for N-(hydroxymethyl)benzamide derivatives bearing electron-donating groups
✍ Scribed by John L. Murphy; William J. Tenn III; Joseph J. Labuda; Richard W. Nagorski
- Book ID
- 104097085
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 248 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Studies of N-(hydroxymethyl)benzamide derivatives have concluded that the hydroxide-dependent reaction occurs via a specific-base catalyzed deprotonation of the hydroxyl group followed by ratedetermining loss of the benzamidate and generation of the aldehyde. The 3-methyl, 4-methyl, and 4-methoxy-N-(hydroxymethyl)benzamide reaction mechanism deviates at higher [HO À ] with amidic hydrolysis becoming competitive and having reaction half-lives of $17 s, in 1 M KOH, I = 1.0 M (KCl), 25 °C. An intramolecular general-base catalyzed mechanism has been suggested for the amidic hydrolysis reaction.