Author(s): Pereira, Fernanda S. [UNESP] ; Nascimento, Heliara D. L. ; Magalhaes, Alvicler ; Peter, Martin G. ; Bataglion, Giovana Anceski ; Eberlin, Marcos N. ; Gonzalez, Eduardo R. P. [UNESP]
Date: 2015
Persistent ID: http://hdl.handle.net/11449/117520
Origin: Oasisbr
Subject(s): chitosan; N-azobenzylchitosan; ESI-MS; GC-MS; SnAr reaction
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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)
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.
Univ Estadual Paulista, Dept Fis Quim & Biol, Programa Posgrad Ciencia & Tecnol Mat POSMAT, Lab Quim Organ Fina CP 467, BR-19060900 Presidente Prudente, Brazil
Univ Campinas UNICAMP, Inst Quim, Lab ThoMSon Espectrometria Massas, BR-13083970 Campinas, SP, Brazil
Univ Campinas UNICAMP, Inst Quim, Dept Quim Inorgan, BR-13083970 Campinas, SP, Brazil
Univ Potsdam, Inst Chem, D-14476 Golm, Germany
Univ Estadual Paulista, Dept Fis Quim & Biol, Programa Posgrad Ciencia & Tecnol Mat POSMAT, Lab Quim Organ Fina CP 467, BR-19060900 Presidente Prudente, Brazil
FAPESP: 06/51987-6
FUNDUNESP: 00355/11-DFP
