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Molecules 2014, 19(11), 17604-17618;

ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan

Laboratório de Química Orgânica Fina—C.P. 467, Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT), Departamento de Física, Química e Biologia, Campus de Presidente Prudente, Universidade Estadual Paulista, Presidente Prudente 19060-900, Brazil
Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil
Departamento de Química Inorgânica, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil
Institut für Chemie, Universität Potsdam, Potsdam D-14476, Germany
Author to whom correspondence should be addressed.
Received: 8 July 2014 / Revised: 15 October 2014 / Accepted: 23 October 2014 / Published: 30 October 2014
(This article belongs to the Special Issue New Trends in Cellulose and Chitin Chemistry)
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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, 1H-NMR and 15N-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. View Full-Text
Keywords: chitosan; N-azobenzylchitosan; ESI-MS; GC-MS; SnAr reaction chitosan; N-azobenzylchitosan; ESI-MS; GC-MS; SnAr reaction

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Pereira, F.S.; Nascimento, H.D.L.; Magalhães, A.; Peter, M.G.; Bataglion, G.A.; Eberlin, M.N.; González, E.R.P. ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan. Molecules 2014, 19, 17604-17618.

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