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ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan
New N-p-chloro-, N-p-bromo-, and N-p-nitrophenylazobenzylchitosan derivatives, as well as the corresponding azophenyl and azophenyl-p-sulfonic acids, were synthesized by coupling N-benzylvchitosan with aryl diazonium salts. The synthesized molecules were analyzed by UV-Vis, FT-IR, (1)H-NMR and (15)N...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271483/ https://www.ncbi.nlm.nih.gov/pubmed/25361424 http://dx.doi.org/10.3390/molecules191117604 |
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author | Pereira, Fernanda S. Nascimento, Heliara D. L. Magalhães, Alviclér Peter, Martin G. Bataglion, Giovana Anceski Eberlin, Marcos N. González, Eduardo R. P. |
author_facet | Pereira, Fernanda S. Nascimento, Heliara D. L. Magalhães, Alviclér Peter, Martin G. Bataglion, Giovana Anceski Eberlin, Marcos N. González, Eduardo R. P. |
author_sort | Pereira, Fernanda S. |
collection | PubMed |
description | New N-p-chloro-, N-p-bromo-, and N-p-nitrophenylazobenzylchitosan derivatives, as well as the corresponding azophenyl and azophenyl-p-sulfonic acids, were synthesized by coupling N-benzylvchitosan with aryl diazonium salts. The synthesized molecules were analyzed by UV-Vis, FT-IR, (1)H-NMR and (15)N-NMR spectroscopy. The capacity of copper chelation by these materials was studied by AAS. Chitosan and the derivatives were subjected to hydrolysis and the products were analyzed by ESI(+)-MS and GC-MS, confirming the formation of N-benzyl chitosan. Furthermore, the MS results indicate that a nucleophilic aromatic substitution (S(n)Ar) reaction occurs under hydrolysis conditions, yielding chloroaniline from N-p-bromo-, and N-p-nitrophenylazo-benzylchitosan as well as bromoaniline from N-p-chloro-, and N-p-nitrophenylazobenzyl-chitosan. |
format | Online Article Text |
id | pubmed-6271483 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62714832019-01-07 ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan Pereira, Fernanda S. Nascimento, Heliara D. L. Magalhães, Alviclér Peter, Martin G. Bataglion, Giovana Anceski Eberlin, Marcos N. González, Eduardo R. P. Molecules Article New N-p-chloro-, N-p-bromo-, and N-p-nitrophenylazobenzylchitosan derivatives, as well as the corresponding azophenyl and azophenyl-p-sulfonic acids, were synthesized by coupling N-benzylvchitosan with aryl diazonium salts. The synthesized molecules were analyzed by UV-Vis, FT-IR, (1)H-NMR and (15)N-NMR spectroscopy. The capacity of copper chelation by these materials was studied by AAS. Chitosan and the derivatives were subjected to hydrolysis and the products were analyzed by ESI(+)-MS and GC-MS, confirming the formation of N-benzyl chitosan. Furthermore, the MS results indicate that a nucleophilic aromatic substitution (S(n)Ar) reaction occurs under hydrolysis conditions, yielding chloroaniline from N-p-bromo-, and N-p-nitrophenylazo-benzylchitosan as well as bromoaniline from N-p-chloro-, and N-p-nitrophenylazobenzyl-chitosan. MDPI 2014-10-30 /pmc/articles/PMC6271483/ /pubmed/25361424 http://dx.doi.org/10.3390/molecules191117604 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Pereira, Fernanda S. Nascimento, Heliara D. L. Magalhães, Alviclér Peter, Martin G. Bataglion, Giovana Anceski Eberlin, Marcos N. González, Eduardo R. P. ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan |
title | ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan |
title_full | ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan |
title_fullStr | ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan |
title_full_unstemmed | ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan |
title_short | ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan |
title_sort | esi(+)-ms and gc-ms study of the hydrolysis of n-azobenzyl derivatives of chitosan |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271483/ https://www.ncbi.nlm.nih.gov/pubmed/25361424 http://dx.doi.org/10.3390/molecules191117604 |
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