title: ESI(+)-MS and GC-MS study of the hydrolysis of N-azobenzyl derivatives of chitosan.
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, 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.
authors.affiliation: Laboratório de Química Orgânica Fina-C.P. 467, Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT), Departamento de Física, Química e Biologia, Campus de Presidente Prudente, Universidade Estadual Paulista, Presidente Prudente 19060-900, Brazil. fernanda.lqof@gmail.com.
authors.forename: Fernanda S
authors.initials: FS
authors.lastname: Pereira
authors.affiliation: Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil. heliara1@hotmail.com.
authors.forename: Heliara D L
authors.initials: HD
authors.lastname: Nascimento
authors.affiliation: Departamento de Química Inorgânica, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil. alvicler@iqm.unicamp.br.
authors.forename: Alviclér
authors.initials: A
authors.lastname: Magalhães
authors.affiliation: Institut für Chemie, Universität Potsdam, Potsdam D-14476, Germany. martin.peter@uni-potsdam.de.
authors.forename: Martin G
authors.initials: MG
authors.lastname: Peter
authors.affiliation: Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil. bataglion@hotmail.com.
authors.forename: Giovana Anceski
authors.initials: GA
authors.lastname: Bataglion
authors.affiliation: Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil. eberlin@iqm.unicamp.br.
authors.forename: Marcos N
authors.initials: MN
authors.lastname: Eberlin
authors.affiliation: Laboratório de Química Orgânica Fina-C.P. 467, Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT), Departamento de Física, Química e Biologia, Campus de Presidente Prudente, Universidade Estadual Paulista, Presidente Prudente 19060-900, Brazil. eperez@fct.unesp.br.
authors.forename: Eduardo R P
authors.initials: ER
authors.lastname: González
mesh_terms: D048271:Chitosan / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods
chemical_list: D048271:Chitosan