《Kinetics and mechanism of reversible, base-catalyzed ring closure of 3-(methoxycarbonyl)propionanilide and (methoxycarbonyl)methyl N-phenylcarbamate》 was written by Kavalek, Jaromir; Machacek, Vladimir; Svobodova, Gabriela; Sterba, Vojeslav. Formula: C8H9NO2 And the article was included in Collection of Czechoslovak Chemical Communications on April 30 ,1989. The article conveys some information:
The rate constants of reversible, base-catalyzed ring closure of 3-(methoxycarbonyl)propionanilide (I) and (methoxycarbonylmethyl) phenylcarbamate (II) to 1-phenyl-2,5-pyrrolidinedione (III) and 3-phenyl-2,4-oxazolidinedione (IV), resp., and the rates of solvolyses of III and IV in water and methanol have been determined In both cases, an equilibrium is established between the starting ester and the cyclization product in methoxide solutions, which is strongly shifted in favor of the starting ester. In the case of II in methoxide solutions, the cyclization is followed by a much slower splitting of the cyclization product to give glycolic acid anilide. The effects of X = NH, CH2, O, S in RNHCOXCH2COOMe on the rates of the cyclization and solvolysis of the cyclization products is discussed.2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Formula: C8H9NO2) was used in this study.
2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Formula: C8H9NO2 The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics