Polymeric catalysis: Imidazoles grafted onto poly(vinylamine). I. Synthesis and grafting of imidazolylalkanoic acids

Abstract

Some ω‐(1‐imidazolyl) and ω‐[4(5)‐imidazolyl]alkanoic acids were synthesized and grafted onto poly(vinylamine) with an amide bond. These water‐soluble grafts were used to study the kinetics of the esterolysis of activated phenyl esters. The 1‐substituted imidazoles were prepared by the reaction of the sodium salt of imidazole with the ethyl ω‐bromoalkanoates. The 4(5)‐substituted imidazoles were prepared from urocanic acid or 4(5)‐hydroxymethylimidazole. The ω‐(1‐imidazolyl)alkanoic acids were grafted onto poly(vinylamine) via their acyl–guanidine derivatives; the 3‐[4(5)‐imidazolyl]propanoic acid was grafted with a water‐soluble carbodiimide.

Synthesis and Catalytic Properties of Imidazole-Functionalized Poly(propylene imine)Dendrimers

“…The history of the use of imidazole-modified polymers for the catalytic hydrolysis of activated esters is quite rich. Particularly relevant to this work are the previous results of Klotz 1,2 and Overberger [3][4][5] who independently demonstrated that imidazole-modified polymers are capable of exhibiting cooperative catalysis in which two neighboring imidazole units served as general-acid/general-base catalysts. Overberger used primarily poly(vinyl imidazoles) while Klotz used primarily poly(ethylene imine) modified with imidazoles.…”