Polymers containing imidazole groups as nanoreactors for hydrolysis of esters

Luciano A. Giusti; Michelle Medeiros; Natasha Londero Ferreira; José R. Mora; Haidi D. Fiedler

doi:10.1002/poc.3263

Polymers containing imidazole groups as nanoreactors for hydrolysis of esters

Luciano A. Giusti
, Michelle Medeiros
, Natasha Londero Ferreira
, José R. Mora
, Haidi D. Fiedler^*

^*Corresponding author for this work

Universidade Federal de Santa Catarina

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

A polymer (PAIM) containing the functional groups imidazole and carboxylic acid acts as a nanoreactor to accelerate deacylation and dephosphorylation reactions. The synthesis was designed to position the two functional groups next to each other, allowing cooperativity. The catalytic efficiency of the polymer was evaluated for the hydrolytic cleavage of p-nitrophenyl acetate (PNPA) and diethyl 2,4-dinitrophenyl phosphate (DEDNPP). PAIM was both efficient and promiscuous, increasing the rates of all reactions up to 10⁷-fold.

Original language	English
Pages (from-to)	297-302
Number of pages	6
Journal	Journal of Physical Organic Chemistry
Volume	27
Issue number	4
DOIs	https://doi.org/10.1002/poc.3263
State	Published - Apr 2014
Externally published	Yes

Keywords

carboxylate esters
catalysis
hydrolysis
phosphate esters
polymers

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10.1002/poc.3263

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@article{eafad7551a3745bf91ec0fa2a98154e2,

title = "Polymers containing imidazole groups as nanoreactors for hydrolysis of esters",

abstract = "A polymer (PAIM) containing the functional groups imidazole and carboxylic acid acts as a nanoreactor to accelerate deacylation and dephosphorylation reactions. The synthesis was designed to position the two functional groups next to each other, allowing cooperativity. The catalytic efficiency of the polymer was evaluated for the hydrolytic cleavage of p-nitrophenyl acetate (PNPA) and diethyl 2,4-dinitrophenyl phosphate (DEDNPP). PAIM was both efficient and promiscuous, increasing the rates of all reactions up to 107-fold.",

keywords = "carboxylate esters, catalysis, hydrolysis, phosphate esters, polymers",

author = "Giusti, \{Luciano A.\} and Michelle Medeiros and Ferreira, \{Natasha Londero\} and Mora, \{Jos{\'e} R.\} and Fiedler, \{Haidi D.\}",

year = "2014",

month = apr,

doi = "10.1002/poc.3263",

language = "Ingl{\'e}s",

volume = "27",

pages = "297--302",

journal = "Journal of Physical Organic Chemistry",

issn = "0894-3230",

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TY - JOUR

T1 - Polymers containing imidazole groups as nanoreactors for hydrolysis of esters

AU - Giusti, Luciano A.

AU - Medeiros, Michelle

AU - Ferreira, Natasha Londero

AU - Mora, José R.

AU - Fiedler, Haidi D.

PY - 2014/4

Y1 - 2014/4

N2 - A polymer (PAIM) containing the functional groups imidazole and carboxylic acid acts as a nanoreactor to accelerate deacylation and dephosphorylation reactions. The synthesis was designed to position the two functional groups next to each other, allowing cooperativity. The catalytic efficiency of the polymer was evaluated for the hydrolytic cleavage of p-nitrophenyl acetate (PNPA) and diethyl 2,4-dinitrophenyl phosphate (DEDNPP). PAIM was both efficient and promiscuous, increasing the rates of all reactions up to 107-fold.

AB - A polymer (PAIM) containing the functional groups imidazole and carboxylic acid acts as a nanoreactor to accelerate deacylation and dephosphorylation reactions. The synthesis was designed to position the two functional groups next to each other, allowing cooperativity. The catalytic efficiency of the polymer was evaluated for the hydrolytic cleavage of p-nitrophenyl acetate (PNPA) and diethyl 2,4-dinitrophenyl phosphate (DEDNPP). PAIM was both efficient and promiscuous, increasing the rates of all reactions up to 107-fold.

KW - carboxylate esters

KW - catalysis

KW - hydrolysis

KW - phosphate esters

KW - polymers

UR - https://www.scopus.com/pages/publications/84897914099

U2 - 10.1002/poc.3263

DO - 10.1002/poc.3263

M3 - Artículo

AN - SCOPUS:84897914099

SN - 0894-3230

VL - 27

SP - 297

EP - 302

JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

IS - 4

ER -

Polymers containing imidazole groups as nanoreactors for hydrolysis of esters

Abstract

Keywords

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