TY  - JOUR
A1  - Pereira, Fernanda S.
A1  - Nascimento, Heliara D. L.
A1  - Magalhaes, Alvicler
A1  - Peter, Martin G.
A1  - Bataglion, Giovana Anceski
A1  - Eberlin, Marcos N.
A1  - Gonzalez, Eduardo R. P.
T1  - ESI(+)-MS and GC-MS study of the hydrolysis of N-azobenzyl derivatives of chitosan
JF  - Molecules
N2  - 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.
KW  - chitosan
KW  - N-azobenzylchitosan
KW  - ESI-MS
KW  - GC-MS
KW  - SnAr reaction
Y1  - 2014
U6  - https://doi.org/10.3390/molecules191117604
SN  - 1420-3049
VL  - 19
IS  - 11
SP  - 17604
EP  - 17618
PB  - MDPI
CY  - Basel
ER  -