Synthesis, spectral characterizations and antimicrobial activity of some Schiff bases of 4-chloro-2-aminophenol

Abstract

A series of 4-chloro-2-[(arylmethylidene)amino]phenols (1–11) including methoxy group were synthesized using appropriate synthetic route. The structures of the Schiff bases were characterized by FT-IR, UV-Vis, ESI-MS, ¹H and ¹³C-NMR spectroscopic techniques and analytical methods. A relation is observed between melting points and existence of intramolecular hydrogen bonding. IR spectra of the compounds including and not including hydrogen bonding were compared. The compounds 2 and 4 show the characteristic UV bands attributed to the NH-forms. According to the ¹H-NMR spectral data the compound 2 has the strongest intramolecular hydrogen bonding and the compound 6 shows two isomeric structure. On the other hand, antibacterial and antifungal activities of the compounds were investigated. Most of the compounds show selective activity toward S. epidermidis and C. albicans.

KEY WORDS: Schiff base, 4-Chloro-2-aminophenol, Antimicrobial activity

Bull. Chem. Soc. Ethiop. 2011, 25(3), 407-417.