Pereira, Fernanda S. [UNESP]Nascimento, Heliara D. L.Magalhaes, AlviclerPeter, Martin G.Bataglion, Giovana AnceskiEberlin, Marcos N.Gonzalez, Eduardo R. P. [UNESP]2015-03-182015-03-182014-11-01Molecules. Basel: Mdpi Ag, v. 19, n. 11, p. 17604-17618, 2014.1420-3049http://hdl.handle.net/11449/117520New 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.17604-17618engchitosanN-azobenzylchitosanESI-MSGC-MSSnAr reactionArtigo10.3390/molecules191117604WOS:000345564300028Acesso abertoWOS000345564300028.pdf