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

Molecules

Fernanda S. Pereira¹  Heliara D. L. Nascimento³  Alviclér Magalh฾s⁴  Martin G. Peter²  Giovana Anceski Bataglion³  Marcos N. Eberlin³  Eduardo R. P. González¹ 

[1] 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; E-Mail:;Institut für Chemie, Universität Potsdam, Potsdam D-14476, Germany; E-Mail:;Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil; E-Mails:;Departamento de Química Inorgânica, Instituto de Química, Universidade de Campinas UNICAMP, Campinas 13083-970, Brazil; E-Mail:

关键词: chitosan;    N-azobenzylchitosan;    ESI-MS;    GC-MS;    S_nAr reaction;   

DOI  :  10.3390/molecules191117604

来源: mdpi

【 摘 要 】

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 (S_nAr) 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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.