Kinetics and Mechanism of the Cleavage of N-Phthaloylglycine in Buffers of Some Primary Amines

Abstract

Kinetic studies on the nucleophilic cleavage of N-phthaloylglycine (NPG) in buffers of 2-methoxyethylamine, and 2-hydroxyethylamine reveal the relationship: knapp = A1 [Am]T/(1 + A2 [Am]T) where A1 and A2 are constants (kinetic parameters) and knapp and [Am]T represent apparent nucleophilic second-order rate constant and total amine buffer concentration, respectively.

The 1:1 adduct of caffeine and 2-(1,3-dioxoisoindolin-2-yl)acetic acid

“…For background to N-phthaloylglycine and its derivatives, see: Antunes et al (1998); Barooah et al (2006a,b); Khan & Ismail (2002); Shariat & Abdollahi (2004); Yunus et al (2008).…”

2-[2-(1,3-Dioxoisoindolin-2-yl)acetamido]acetic acid

“…Among phthalimides derivatives, N-phthaloylglycine has been the most widely studied for its metal complexes with supramolecular structures (Barooah et al, 2006), kinetic studies for cleavage with various amines (Khan & Ismail, 2002) and heterocyclic derivatives such as oxadiazole (Antunes et al, 1998) and 1,2,4-triazole (Yunus et al, 2008). In the present investigation we report on the crystal structure of an acetamide derivative of the N-phthaloylglycine moiety.…”

“…For the structures and biological properties of phthalimides and various derivatives, see: Antunes et al (1998); Barooah & Baruah (2007); Barooah et al (2006); Khan et al (2002); Sharma et al (2010); Yunus et al (2008). For standard bond lengths, see: Allen et al (1987).…”

catena-Poly[[diaquacalcium]bis[μ-2-(1,3-dioxoisoindolin-2-yl)acetato]-κ3O,O′:O;κ3O:O,O′]

“…For background to N-phthaloylglycine, see: Khan & Ismail (2002). For related structures, see: Barooah et al (2006).…”

“…SS is grateful to the University of Hong Kong for providing facilities for crystallographic studies. N-Phthaloylglycine is a simple N-phthaloylamino acid which has been widely studied for cleavage with various amines (Khan & Ismail, 2002) and metal complexation with interesting supramolecular structures (Barooah et al, 2006). In an attempt to synthesis calcium(II) complex of N-phthaloylglycine, we have prepared a calcium complex of Nphthaloylglycine as the title compound and studied it crystal structure which is presented in this article.…”