MULTIFUNCTIONAL HYDROLYTIC CATALYSES - 9. HYDROLYSIS OF p-NITROPHENYL ACETATE BY BIFUNCTIONAL POLYMER CATALYSTS CONTAINING ZWITTERIONIC (HYDROXAMATE) NUCLEOPHILES.

Yoshio Okahata, Toyoki Kunitake

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

In the reported experiments, the hydrolysis of p-nitrophenyl acetate by bifunctional polymer catalysts was studied in 28. 9% EtOH-H//2O at 30 degree C. Partial (ca. 10 mole%) quaternization of poly(4-vinylpyridine) and poly(1-vinyl-2-ethylimidazole) with benzyl N-benzyl chloroacetohydroxamate and the subsequent removal of the benzyl group produced water-soluble polymers containing zwitterionic hydroxamate groups and free pyridine (or imidazole) groups. The zwitterionic hydroxamate was a nucleophile more than 10 times as effective as simple hydroxamate anions, and the acetyl hydroxamate intermediate was efficiently hydrolyzed by the intrapolymeric pyridine (or imidazole) group. Thus, the catalytic efficiency of these bifunctional polymers was much better than monofunctional polymers which contain either hydroxamate or imidazole, and amounted to 10-20% of that of alpha -chymotrypsin under a comparable condition.

Original languageEnglish
Pages (from-to)2571-2586
Number of pages16
JournalJ Polym Sci Polym Chem Ed
Volume15
Issue number11
Publication statusPublished - Jan 1 1977
Externally publishedYes

Fingerprint

Nucleophiles
Hydrolysis
Catalysts
Polymers
Pyridine
Negative ions
Experiments

All Science Journal Classification (ASJC) codes

  • Engineering(all)

Cite this

MULTIFUNCTIONAL HYDROLYTIC CATALYSES - 9. HYDROLYSIS OF p-NITROPHENYL ACETATE BY BIFUNCTIONAL POLYMER CATALYSTS CONTAINING ZWITTERIONIC (HYDROXAMATE) NUCLEOPHILES. / Okahata, Yoshio; Kunitake, Toyoki.

In: J Polym Sci Polym Chem Ed, Vol. 15, No. 11, 01.01.1977, p. 2571-2586.

Research output: Contribution to journalArticle

@article{cd6d5bed6768412582d1c775202f435b,
title = "MULTIFUNCTIONAL HYDROLYTIC CATALYSES - 9. HYDROLYSIS OF p-NITROPHENYL ACETATE BY BIFUNCTIONAL POLYMER CATALYSTS CONTAINING ZWITTERIONIC (HYDROXAMATE) NUCLEOPHILES.",
abstract = "In the reported experiments, the hydrolysis of p-nitrophenyl acetate by bifunctional polymer catalysts was studied in 28. 9{\%} EtOH-H//2O at 30 degree C. Partial (ca. 10 mole{\%}) quaternization of poly(4-vinylpyridine) and poly(1-vinyl-2-ethylimidazole) with benzyl N-benzyl chloroacetohydroxamate and the subsequent removal of the benzyl group produced water-soluble polymers containing zwitterionic hydroxamate groups and free pyridine (or imidazole) groups. The zwitterionic hydroxamate was a nucleophile more than 10 times as effective as simple hydroxamate anions, and the acetyl hydroxamate intermediate was efficiently hydrolyzed by the intrapolymeric pyridine (or imidazole) group. Thus, the catalytic efficiency of these bifunctional polymers was much better than monofunctional polymers which contain either hydroxamate or imidazole, and amounted to 10-20{\%} of that of alpha -chymotrypsin under a comparable condition.",
author = "Yoshio Okahata and Toyoki Kunitake",
year = "1977",
month = "1",
day = "1",
language = "English",
volume = "15",
pages = "2571--2586",
journal = "Journal of polymer science. Part A-1, Polymer chemistry",
issn = "0449-296X",
publisher = "Interscience Publishers",
number = "11",

}

TY - JOUR

T1 - MULTIFUNCTIONAL HYDROLYTIC CATALYSES - 9. HYDROLYSIS OF p-NITROPHENYL ACETATE BY BIFUNCTIONAL POLYMER CATALYSTS CONTAINING ZWITTERIONIC (HYDROXAMATE) NUCLEOPHILES.

AU - Okahata, Yoshio

AU - Kunitake, Toyoki

PY - 1977/1/1

Y1 - 1977/1/1

N2 - In the reported experiments, the hydrolysis of p-nitrophenyl acetate by bifunctional polymer catalysts was studied in 28. 9% EtOH-H//2O at 30 degree C. Partial (ca. 10 mole%) quaternization of poly(4-vinylpyridine) and poly(1-vinyl-2-ethylimidazole) with benzyl N-benzyl chloroacetohydroxamate and the subsequent removal of the benzyl group produced water-soluble polymers containing zwitterionic hydroxamate groups and free pyridine (or imidazole) groups. The zwitterionic hydroxamate was a nucleophile more than 10 times as effective as simple hydroxamate anions, and the acetyl hydroxamate intermediate was efficiently hydrolyzed by the intrapolymeric pyridine (or imidazole) group. Thus, the catalytic efficiency of these bifunctional polymers was much better than monofunctional polymers which contain either hydroxamate or imidazole, and amounted to 10-20% of that of alpha -chymotrypsin under a comparable condition.

AB - In the reported experiments, the hydrolysis of p-nitrophenyl acetate by bifunctional polymer catalysts was studied in 28. 9% EtOH-H//2O at 30 degree C. Partial (ca. 10 mole%) quaternization of poly(4-vinylpyridine) and poly(1-vinyl-2-ethylimidazole) with benzyl N-benzyl chloroacetohydroxamate and the subsequent removal of the benzyl group produced water-soluble polymers containing zwitterionic hydroxamate groups and free pyridine (or imidazole) groups. The zwitterionic hydroxamate was a nucleophile more than 10 times as effective as simple hydroxamate anions, and the acetyl hydroxamate intermediate was efficiently hydrolyzed by the intrapolymeric pyridine (or imidazole) group. Thus, the catalytic efficiency of these bifunctional polymers was much better than monofunctional polymers which contain either hydroxamate or imidazole, and amounted to 10-20% of that of alpha -chymotrypsin under a comparable condition.

UR - http://www.scopus.com/inward/record.url?scp=0017552209&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0017552209&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0017552209

VL - 15

SP - 2571

EP - 2586

JO - Journal of polymer science. Part A-1, Polymer chemistry

JF - Journal of polymer science. Part A-1, Polymer chemistry

SN - 0449-296X

IS - 11

ER -