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, H-1 and C-13-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 H-1-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.