ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.3390/molecules191117604 http://hdl.handle.net/11449/117520 |
Resumo: | 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, H-1-NMR and N-15-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 (SnAr) 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. |
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ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of ChitosanchitosanN-azobenzylchitosanESI-MSGC-MSSnAr reactionNew 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, H-1-NMR and N-15-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 (SnAr) 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.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Programa de Pos-graduacao em Ciencia e Tecnologia de Materiais (POSMAT)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação para o Desenvolvimento da UNESP (FUNDUNESP)Univ Estadual Paulista, Dept Fis Quim & Biol, Programa Posgrad Ciencia & Tecnol Mat POSMAT, Lab Quim Organ Fina CP 467, BR-19060900 Presidente Prudente, BrazilUniv Campinas UNICAMP, Inst Quim, Lab ThoMSon Espectrometria Massas, BR-13083970 Campinas, SP, BrazilUniv Campinas UNICAMP, Inst Quim, Dept Quim Inorgan, BR-13083970 Campinas, SP, BrazilUniv Potsdam, Inst Chem, D-14476 Golm, GermanyUniv Estadual Paulista, Dept Fis Quim & Biol, Programa Posgrad Ciencia & Tecnol Mat POSMAT, Lab Quim Organ Fina CP 467, BR-19060900 Presidente Prudente, BrazilFAPESP: 06/51987-6FUNDUNESP: 00355/11-DFPMdpi AgUniversidade Estadual Paulista (Unesp)Universidade Estadual de Campinas (UNICAMP)Univ PotsdamPereira, Fernanda S. [UNESP]Nascimento, Heliara D. L.Magalhaes, AlviclerPeter, Martin G.Bataglion, Giovana AnceskiEberlin, Marcos N.Gonzalez, Eduardo R. P. [UNESP]2015-03-18T15:56:21Z2015-03-18T15:56:21Z2014-11-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article17604-17618application/pdfhttp://dx.doi.org/10.3390/molecules191117604Molecules. Basel: Mdpi Ag, v. 19, n. 11, p. 17604-17618, 2014.1420-3049http://hdl.handle.net/11449/11752010.3390/molecules191117604WOS:000345564300028WOS000345564300028.pdfWeb of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengMolecules3.0980,855info:eu-repo/semantics/openAccess2024-06-19T12:44:41Zoai:repositorio.unesp.br:11449/117520Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T20:23:12.981820Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
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 |
spellingShingle |
ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan Pereira, Fernanda S. [UNESP] chitosan N-azobenzylchitosan ESI-MS GC-MS SnAr reaction |
title_short |
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_sort |
ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan |
author |
Pereira, Fernanda S. [UNESP] |
author_facet |
Pereira, Fernanda S. [UNESP] Nascimento, Heliara D. L. Magalhaes, Alvicler Peter, Martin G. Bataglion, Giovana Anceski Eberlin, Marcos N. Gonzalez, Eduardo R. P. [UNESP] |
author_role |
author |
author2 |
Nascimento, Heliara D. L. Magalhaes, Alvicler Peter, Martin G. Bataglion, Giovana Anceski Eberlin, Marcos N. Gonzalez, Eduardo R. P. [UNESP] |
author2_role |
author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) Universidade Estadual de Campinas (UNICAMP) Univ Potsdam |
dc.contributor.author.fl_str_mv |
Pereira, Fernanda S. [UNESP] Nascimento, Heliara D. L. Magalhaes, Alvicler Peter, Martin G. Bataglion, Giovana Anceski Eberlin, Marcos N. Gonzalez, Eduardo R. P. [UNESP] |
dc.subject.por.fl_str_mv |
chitosan N-azobenzylchitosan ESI-MS GC-MS SnAr reaction |
topic |
chitosan N-azobenzylchitosan ESI-MS GC-MS SnAr reaction |
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, H-1-NMR and N-15-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 (SnAr) 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. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-11-01 2015-03-18T15:56:21Z 2015-03-18T15:56:21Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.3390/molecules191117604 Molecules. Basel: Mdpi Ag, v. 19, n. 11, p. 17604-17618, 2014. 1420-3049 http://hdl.handle.net/11449/117520 10.3390/molecules191117604 WOS:000345564300028 WOS000345564300028.pdf |
url |
http://dx.doi.org/10.3390/molecules191117604 http://hdl.handle.net/11449/117520 |
identifier_str_mv |
Molecules. Basel: Mdpi Ag, v. 19, n. 11, p. 17604-17618, 2014. 1420-3049 10.3390/molecules191117604 WOS:000345564300028 WOS000345564300028.pdf |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Molecules 3.098 0,855 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
17604-17618 application/pdf |
dc.publisher.none.fl_str_mv |
Mdpi Ag |
publisher.none.fl_str_mv |
Mdpi Ag |
dc.source.none.fl_str_mv |
Web of Science reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808129195545460736 |