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A series of 4-chloro-2-[(arylmethylidene)amino]phenols (<b>1</b>–<b>11</b>) 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 <b>2</b> and <b>4</b> show the characteristic UV bands attributed to the NH-forms. According to the ¹H-NMR spectral data the compound <b>2</b> has the strongest intramolecular hydrogen bonding and the compound <b>6</b> 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 <i>S. epidermidis</i> and <i>C. albicans</i>.