Hydrolysis of naptalam and structurally related amides: inhibition by dissolved metal ions and metal (hydr)oxide surfaces was written by Huang, Ching-Hua;Stone, Alan T.. And the article was included in Journal of Agricultural and Food Chemistry in 1999.Synthetic Route of C11H15NO2 This article mentions the following:
In metal ion-free solutions, the secondary amide naptalam hydrolyzes more rapidly as the pH is decreased; intramol. nucleophilic attack by a carboxylate side group is very likely involved. Millimolar levels of dissolved CuII and ZnII inhibit hydrolysis between pH 3.6 and pH 6.5. Metal ion-naptalam complex formation is important since addition of the competitive ligand citrate lessens the inhibitory effect. The metal (hydr)oxide surfaces Al2O3 and FeOOH inhibit naptalam hydrolysis to a lesser degree; inhibition is proportional to the extent of naptalam adsorbed. Secondary amides (propanil, salicylanilide, and N-1-naphthylacetamide) and tertiary amides (N-methyl-N-1-naphthylacetamide, furalaxyl, and N,N-diethylsalicylamide) that lack carboxylate side groups do not hydrolyze within 45 days of reaction, even when millimolar CuII concentrations are present. Tertiary amides possessing carboxylate side groups (N,N-diethyl-3,6-difluorophthalamic acid and N,N-dimethylsuccinamic acid) do hydrolyze but are insensitive to the presence or absence of CuII. The inhibitory effect is believed to occur via metal coordination of (1) the carbonyl group of naptalam, which induces deprotonation of the amide group and makes the substrate less reactive toward nucleophilic attack; (2) the free carboxylate group of naptalam, which blocks intramol. nucleophilic attack; or (3) a combination of the two. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Synthetic Route of C11H15NO2).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Synthetic Route of C11H15NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics