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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.
Author details: | Fernanda S. Pereira, Heliara D. L. Nascimento, Alvicler Magalhaes, Martin G. Peter, Giovana Anceski Bataglion, Marcos N. Eberlin, Eduardo R. P. Gonzalez |
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DOI: | https://doi.org/10.3390/molecules191117604 |
ISSN: | 1420-3049 |
Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/25361424 |
Title of parent work (English): | Molecules |
Publisher: | MDPI |
Place of publishing: | Basel |
Publication type: | Article |
Language: | English |
Year of first publication: | 2014 |
Publication year: | 2014 |
Release date: | 2017/03/27 |
Tag: | ESI-MS; GC-MS; N-azobenzylchitosan; SnAr reaction; chitosan |
Volume: | 19 |
Issue: | 11 |
Number of pages: | 15 |
First page: | 17604 |
Last Page: | 17618 |
Funding institution: | 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 |
Publishing method: | Open Access |