Synthesis of polymer catalysts containing vinyl-imidazolehydroxamic acid and their ester hydrolysis catalytic activity

Hiroyuki Nishide, Winfried Storck, Georg Manecke

研究成果: Article

3 引用 (Scopus)

抄録

The hydrolysis of p-nitrophenyl acetate catalyzed by polymers containing imidazole-4-carbohydroxamic acid has been studied. Radical homo-and copolymerization of the protected vinyl monomer, N-methyl-(1-vinyl-imidazole-4)-carbohydroxamic acid benzyl ester (3a), and the subsequent removal of the benzyl group, produced water-soluble polymers containing the imidazole-4-carbohydroxamic acid group. The hydrolysis of p-nitro-phenylacetate catalyzed by the imidazole-4-carbohydroxamic acid derivatives was analyzed by burst kinetics and proceeded faster than did that catalyzed by imidazoles or carbohydroxamic acid. The catalytic activity of the polymer was less than that of the monomeric analogue. The observed rate constant of acylation was proportional to the dissociation degree of the carbohydroxamic acid group and was especially low in the negatively charged polymer 13a. On the other hand, the acylation was favourable to the positively charged polymer catalyst 13c due to its lower pKa value, but the de-acylation process was retarded.

元の言語English
ページ(範囲)23-39
ページ数17
ジャーナルJournal of Molecular Catalysis
6
発行部数1
DOI
出版物ステータスPublished - 1979
外部発表Yes

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Hydrolysis
Catalyst activity
Esters
Polymers
Acylation
Catalysts
Acids
Imidazoles
Copolymerization
Rate constants
Monomers
Derivatives
Kinetics
imidazole
Water

ASJC Scopus subject areas

  • Engineering(all)
  • Medicine(all)

これを引用

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abstract = "The hydrolysis of p-nitrophenyl acetate catalyzed by polymers containing imidazole-4-carbohydroxamic acid has been studied. Radical homo-and copolymerization of the protected vinyl monomer, N-methyl-(1-vinyl-imidazole-4)-carbohydroxamic acid benzyl ester (3a), and the subsequent removal of the benzyl group, produced water-soluble polymers containing the imidazole-4-carbohydroxamic acid group. The hydrolysis of p-nitro-phenylacetate catalyzed by the imidazole-4-carbohydroxamic acid derivatives was analyzed by burst kinetics and proceeded faster than did that catalyzed by imidazoles or carbohydroxamic acid. The catalytic activity of the polymer was less than that of the monomeric analogue. The observed rate constant of acylation was proportional to the dissociation degree of the carbohydroxamic acid group and was especially low in the negatively charged polymer 13a. On the other hand, the acylation was favourable to the positively charged polymer catalyst 13c due to its lower pKa value, but the de-acylation process was retarded.",
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AU - Storck, Winfried

AU - Manecke, Georg

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N2 - The hydrolysis of p-nitrophenyl acetate catalyzed by polymers containing imidazole-4-carbohydroxamic acid has been studied. Radical homo-and copolymerization of the protected vinyl monomer, N-methyl-(1-vinyl-imidazole-4)-carbohydroxamic acid benzyl ester (3a), and the subsequent removal of the benzyl group, produced water-soluble polymers containing the imidazole-4-carbohydroxamic acid group. The hydrolysis of p-nitro-phenylacetate catalyzed by the imidazole-4-carbohydroxamic acid derivatives was analyzed by burst kinetics and proceeded faster than did that catalyzed by imidazoles or carbohydroxamic acid. The catalytic activity of the polymer was less than that of the monomeric analogue. The observed rate constant of acylation was proportional to the dissociation degree of the carbohydroxamic acid group and was especially low in the negatively charged polymer 13a. On the other hand, the acylation was favourable to the positively charged polymer catalyst 13c due to its lower pKa value, but the de-acylation process was retarded.

AB - The hydrolysis of p-nitrophenyl acetate catalyzed by polymers containing imidazole-4-carbohydroxamic acid has been studied. Radical homo-and copolymerization of the protected vinyl monomer, N-methyl-(1-vinyl-imidazole-4)-carbohydroxamic acid benzyl ester (3a), and the subsequent removal of the benzyl group, produced water-soluble polymers containing the imidazole-4-carbohydroxamic acid group. The hydrolysis of p-nitro-phenylacetate catalyzed by the imidazole-4-carbohydroxamic acid derivatives was analyzed by burst kinetics and proceeded faster than did that catalyzed by imidazoles or carbohydroxamic acid. The catalytic activity of the polymer was less than that of the monomeric analogue. The observed rate constant of acylation was proportional to the dissociation degree of the carbohydroxamic acid group and was especially low in the negatively charged polymer 13a. On the other hand, the acylation was favourable to the positively charged polymer catalyst 13c due to its lower pKa value, but the de-acylation process was retarded.

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