Synthesis, spectroscopic characterization and pH dependent photometric and electrochemical fate of Schiff bases.

Abdur Rauf, Afzal Shah, Saghir Abbas, Usman Ali Rana, Salah Ud-Din Khan, Saqib Ali, Rumana Qureshi, Heinz-Bernhard Kraatz, Francine Belanger-Gariepy

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 2015;138():58-66

PMID: 25437845

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Abstract

A new Schiff base, 1-((4-bromophenylimino) methyl) naphthalen-2-ol (BPIMN) was successfully synthesized and characterized by (1)H NMR, (13)C NMR, FTIR and UV-Vis spectroscopy. The results were compared with a structurally related Schiff base, 1-((4-chlorophenylimino) methyl) naphthalen-2-ol (CPIMN). The photometric and electrochemical fate of BPIMN and CPIMN was investigated in a wide pH range. The experimental findings were supported by quantum mechanical approach. The redox mechanistic pathways were proposed on the basis of results obtained electrochemical techniques. Moreover, pH dependent UV-Vis spectroscopy of BPIMN and CPIMN was carried out and the appearance of isosbestic points indicated the existence of these compounds in different tautomeric forms.

Address: Department of Chemistry, Quaid-i-Azam University, 45320 Islamabad, Pakistan.; Department of Chemistry, Quaid-i-Azam University, 45320 Islamabad, Pakistan; Department of Physical and Environmental Sciences, University of Toronto Scarborough, 1265 Military Trail, Toronto M1C 1A4, Canada. Electronic address: [email protected].; Deanship of Scientific Research, College of Engineering, King Saud University, Riyadh 11421, Saudi Arabia.; Department of Physical and Environmental Sciences, University of Toronto Scarborough, 1265 Military Trail, Toronto M1C 1A4, Canada.; Department de Chimie, Universite de Montreal, Montreal, Canada.

DOI: 10.1016/j.saa.2014.10.111

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MeSH Terms: Electrochemical Techniques, Halogenation, Hydrogen-Ion Concentration, Magnetic Resonance Spectroscopy, Methylation, Models, Molecular, Naphthalenes, Oxidation-Reduction, Photometry, Schiff Bases, Spectrophotometry, Ultraviolet, Spectroscopy, Fourier Transform Infrared, Stereoisomerism