@article{PereiraNascimentoMagalhaesetal.2014,
  author    = {Pereira, Fernanda S. and Nascimento, Heliara D. L. and Magalhaes, Alvicler and Peter, Martin G. and Bataglion, Giovana Anceski and Eberlin, Marcos N. and Gonzalez, Eduardo R. P.},
  title     = {ESI(+)-MS and GC-MS study of the hydrolysis of N-azobenzyl derivatives of chitosan},
  series = {Molecules},
  volume    = {19},
  journal   = {Molecules},
  number    = {11},
  publisher = {MDPI},
  address   = {Basel},
  issn      = {1420-3049},
  doi       = {10.3390/molecules191117604},
  pages     = {17604 -- 17618},
  year      = {2014},
  abstract  = {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.},
  language  = {en}
}