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, 1H-NMR and 15N-NMR...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2014-10, Vol.19 (11), p.17604-17618
Main Authors: Pereira, Fernanda S, Nascimento, Heliara D L, Magalhães, Alviclér, Peter, Martin G, Bataglion, Giovana Anceski, Eberlin, Marcos N, González, Eduardo R P
Format: Article
Language:English
Subjects:
chitosan
Chitosan - chemistry
ESI-MS
Gas Chromatography-Mass Spectrometry - methods
GC-MS
Hydrolysis
Information storage
Magnetic Resonance Spectroscopy - methods
Molecular Structure
N-azobenzylchitosan
Polymers
SnAr reaction
Spectroscopy, Fourier Transform Infrared - methods
Spectrum analysis
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules191117604