ESI(+)-MS and GC-MS Study of the Hydrolysis of N-Azobenzyl Derivatives of Chitosan

Author(s)

Pereira, Fernanda S. ^[1] ; Nascimento, Heliara D. L. ^[2] ; Magalhaes, Alvicler ^[3] ; Peter, Martin G. ^[4] ; Bataglion, Giovana Anceski ^[2] ; Eberlin, Marcos N. ^[2] ; Gonzalez, Eduardo R. P. ^[1]

Affiliation

^[1] Univ Estadual Paulista, Dept Fis Quim & Biol, Programa Posgrad Ciencia & Tecnol Mat POSMAT, Lab Quim Organ Fina CP 467, BR-19060900 Presidente Prudente - Brazil

^[2] Univ Campinas UNICAMP, Inst Quim, Lab ThoMSon Espectrometria Massas, BR-13083970 Campinas, SP - Brazil

^[3] Univ Campinas UNICAMP, Inst Quim, Dept Quim Inorgan, BR-13083970 Campinas, SP - Brazil

^[4] Univ Potsdam, Inst Chem, D-14476 Golm - Germany

• Document type: Journal article
• Source: Molecules; v. 19, n. 11, p. 17604-17618, NOV 2014.
• Web of Science Citations: 1

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. (AU)

• FAPESP's process: 06/51987-6 - Study of the carbon dioxide molecule attachment and activation with nitrogen bases
• Grantee: Eduardo Rene Perez Gonzalez
• Support Opportunities: Research Grants - Young Investigators Grants