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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, 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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Author:Fernanda S. Pereira, Heliara D. L. Nascimento, Alvicler Magalhaes, Martin G. Peter, Giovana Anceski Bataglion, Marcos N. Eberlin, Eduardo R. P. Gonzalez
ISSN:1420-3049 (print)
Pubmed Id:http://www.ncbi.nlm.nih.gov/pubmed?term=25361424
Parent Title (English):Molecules
Place of publication:Basel
Document Type:Article
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
Tag:ESI-MS; GC-MS; N-azobenzylchitosan; SnAr reaction; chitosan
First Page:17604
Last Page:17618
Funder:Fundacao de Apoio a Pesquisa do Estado de Sao Paulo (FAPESP); Programa de Pos-graduacao em Ciencia e Tecnologia de Materiais (POSMAT); Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES); FAPESP [2006/51987-6]; Fundunesp [00355/11-DFP]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert
Publication Way:Open Access