Multifunctional Hydrolytic Catalyses. 8. Remarkable Acceleration of the Hydrolysis of p-Nitrophenyl Acetate by Micellar Bifunctional Catalysts

Toyoki Kunitake, Yoshio Okahata, Tetsuo Sakamoto

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

Surfactant molecules which contain the hydroxamate and imidazole functions were synthesized, and their catalytic actions in aqueous cetyltrimethylammonium bromide micelles were examined for the hydrolysis of p-nitrophenyl acetate at 30 °C. The catalysis proceeded mainly via acylation and imidazole-catalyzed deacylation at the hydroxamate group. Both of these processes were remarkably accelerated in the case of bifunctional micelles, due to activation of anionic nucleophiles in cationic micellar environments. The overall catalytic efficiency exceeded even that of α-chymotrypsin at pH 8 and was more than 5000 times higher than that of imidazole. Micellar monofunctional catalysts and a nonmicellar bifunctional catalyst were much less effective. Therefore, the combination of bifunctionality and micellar microenvironments was essential for the highly efficient catalysis.

Original languageEnglish
Pages (from-to)7799-7806
Number of pages8
JournalJournal of the American Chemical Society
Volume98
Issue number24
DOIs
Publication statusPublished - Nov 1 1976

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Micelles
Catalysis
Hydrolysis
Acylation
Nucleophiles
Catalysts
Surface active agents
Chemical activation
Chymotrypsin
Surface-Active Agents
Molecules
4-nitrophenyl acetate
imidazole
cetrimonium

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Multifunctional Hydrolytic Catalyses. 8. Remarkable Acceleration of the Hydrolysis of p-Nitrophenyl Acetate by Micellar Bifunctional Catalysts. / Kunitake, Toyoki; Okahata, Yoshio; Sakamoto, Tetsuo.

In: Journal of the American Chemical Society, Vol. 98, No. 24, 01.11.1976, p. 7799-7806.

Research output: Contribution to journalArticle

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