Fe-polyaniline composite nanofiber catalyst for chemoselective hydrolysis of oxime

Sanjit Kumar Mahato; Madhumita Bhaumik; Arun Maji; Abhijit Dutta; Debabrata Maiti; Arjun Maity

doi:10.1016/j.jcis.2017.11.059

Fe-polyaniline composite nanofiber catalyst for chemoselective hydrolysis of oxime

Sanjit Kumar Mahato, Madhumita Bhaumik, Arun Maji, Abhijit Dutta, Debabrata Maiti, Arjun Maity

Pharmaceutical Sciences

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

14 Scopus citations

Abstract

A facile chemoselective one-pot strategy for the deprotection of oxime has been developed using Fe⁰-polyaniline composite nanofiber (Fe⁰-PANI), as a catalyst. Nano material based Fe⁰-PANI catalyst has been synthesized via in-situ polymerization of ANI monomer and followed by reductive deposition of Fe⁰ onto PANI matrix. The catalyst was characterized by FE-SEM, HR-TEM, BET, XRD, ATR-FTIR, XPS and VSM techniques. The scope of the transformation was studied for aryl, alkyl and heteroarylketoxime with excellent chemoselectivity (>99%). Mechanistic investigations suggested the involvement of a cationic intermediate with Fe³⁺ active catalytic species. Substituent effect showed a linear free energy relationship. The activation energy (E_a) was calculated to be 17.46 kJ mol⁻¹ for acetophenone oxime to acetophenone conversion. The recyclability of the catalyst demonstrated up to 10 cycles without any significant loss of efficiency. Based on the preliminary experiments a plausible mechanism has been proposed involving a carbocationic intermediate.

Original language	English
Pages (from-to)	592-601
Number of pages	10
Journal	Journal of Colloid and Interface Science
Volume	513
DOIs	https://doi.org/10.1016/j.jcis.2017.11.059
State	Published - Mar 1 2018

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Inc.

Funding

S.K.M. thanks the University of South Africa (UNISA) for Post-Doctoral Fellowship Award. D.M. thanks DST-India (SR/NM/NS-1065/2015) for financial support. Fellowship received from CSIR-India (A. M) is gratefully acknowledged. Thanks to DST/CSIR National Centre for Nano Structured Material and Prof. Gerda Fouche of CSIR-Bioscience Pretoria, South Africa for providing the infrastructure. Nanostructured materials characterization unit is also acknowledged for materials characterization.

Funders	Funder number
CSIR - Central Food Technological Research Institute India
DST-India	SR/NM/NS-1065/2015
University of South Africa

Keywords

Chemoselective
Composite
Hydrolysis
Nanofiber
Oxime
Polyaniline

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Biomaterials
Surfaces, Coatings and Films
Colloid and Surface Chemistry

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title = "Fe-polyaniline composite nanofiber catalyst for chemoselective hydrolysis of oxime",

abstract = "A facile chemoselective one-pot strategy for the deprotection of oxime has been developed using Fe0-polyaniline composite nanofiber (Fe0-PANI), as a catalyst. Nano material based Fe0-PANI catalyst has been synthesized via in-situ polymerization of ANI monomer and followed by reductive deposition of Fe0 onto PANI matrix. The catalyst was characterized by FE-SEM, HR-TEM, BET, XRD, ATR-FTIR, XPS and VSM techniques. The scope of the transformation was studied for aryl, alkyl and heteroarylketoxime with excellent chemoselectivity (>99\%). Mechanistic investigations suggested the involvement of a cationic intermediate with Fe3+ active catalytic species. Substituent effect showed a linear free energy relationship. The activation energy (Ea) was calculated to be 17.46 kJ mol−1 for acetophenone oxime to acetophenone conversion. The recyclability of the catalyst demonstrated up to 10 cycles without any significant loss of efficiency. Based on the preliminary experiments a plausible mechanism has been proposed involving a carbocationic intermediate.",

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author = "Mahato, \{Sanjit Kumar\} and Madhumita Bhaumik and Arun Maji and Abhijit Dutta and Debabrata Maiti and Arjun Maity",

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year = "2018",

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doi = "10.1016/j.jcis.2017.11.059",

language = "English",

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AU - Mahato, Sanjit Kumar

AU - Bhaumik, Madhumita

AU - Maji, Arun

AU - Dutta, Abhijit

AU - Maiti, Debabrata

AU - Maity, Arjun

PY - 2018/3/1

Y1 - 2018/3/1

N2 - A facile chemoselective one-pot strategy for the deprotection of oxime has been developed using Fe0-polyaniline composite nanofiber (Fe0-PANI), as a catalyst. Nano material based Fe0-PANI catalyst has been synthesized via in-situ polymerization of ANI monomer and followed by reductive deposition of Fe0 onto PANI matrix. The catalyst was characterized by FE-SEM, HR-TEM, BET, XRD, ATR-FTIR, XPS and VSM techniques. The scope of the transformation was studied for aryl, alkyl and heteroarylketoxime with excellent chemoselectivity (>99%). Mechanistic investigations suggested the involvement of a cationic intermediate with Fe3+ active catalytic species. Substituent effect showed a linear free energy relationship. The activation energy (Ea) was calculated to be 17.46 kJ mol−1 for acetophenone oxime to acetophenone conversion. The recyclability of the catalyst demonstrated up to 10 cycles without any significant loss of efficiency. Based on the preliminary experiments a plausible mechanism has been proposed involving a carbocationic intermediate.

AB - A facile chemoselective one-pot strategy for the deprotection of oxime has been developed using Fe0-polyaniline composite nanofiber (Fe0-PANI), as a catalyst. Nano material based Fe0-PANI catalyst has been synthesized via in-situ polymerization of ANI monomer and followed by reductive deposition of Fe0 onto PANI matrix. The catalyst was characterized by FE-SEM, HR-TEM, BET, XRD, ATR-FTIR, XPS and VSM techniques. The scope of the transformation was studied for aryl, alkyl and heteroarylketoxime with excellent chemoselectivity (>99%). Mechanistic investigations suggested the involvement of a cationic intermediate with Fe3+ active catalytic species. Substituent effect showed a linear free energy relationship. The activation energy (Ea) was calculated to be 17.46 kJ mol−1 for acetophenone oxime to acetophenone conversion. The recyclability of the catalyst demonstrated up to 10 cycles without any significant loss of efficiency. Based on the preliminary experiments a plausible mechanism has been proposed involving a carbocationic intermediate.

KW - Chemoselective

KW - Composite

KW - Hydrolysis

KW - Nanofiber

KW - Oxime

KW - Polyaniline

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Fe-polyaniline composite nanofiber catalyst for chemoselective hydrolysis of oxime

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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