ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan
AbstractNew 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
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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.
Pereira FS, Nascimento HDL, Magalhães A, Peter MG, Bataglion GA, Eberlin MN, González ERP. ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan. Molecules. 2014; 19(11):17604-17618.Chicago/Turabian Style
Pereira, Fernanda S.; Nascimento, Heliara D.L.; Magalhães, Alviclér; Peter, Martin G.; Bataglion, Giovana A.; Eberlin, Marcos N.; González, Eduardo R.P. 2014. "ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan." Molecules 19, no. 11: 17604-17618.