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Synthesis, Characterization and Crystal Structure of a New Schiff Base Ligand from a Bis(Thiazoline) Template and Hydrolytic Cleavage of the Imine Bond Induced by a Co(II) Cation


Affiliations
1 Kharazmi University, Tehran, Iran, Islamic Republic of
2 Department of Chemistry, University of California, Davis, CA, United States
 

The reaction of bis-[2-amino-4-pheny1-5-thiazolyl] disulfide with 5-nitro-salicylaldehyde in absolute ethanol resulted in the formation of a new Schiff base ligand H2L (1). Characterization of the ligand was performed by FT-IR, 1H NMR, 13C NMR, UV-Vis, elemental analysis and single crystal X-ray diffraction. The ligand, (1), possesses a disulfide -S-S- bridge of 2.1121 (3) Å length, and the molecule adopts a cis-conformation around this bond. In the crystal structure of (1), an intramolecular O-H···N hydrogen bond with D… A distance of 2.69 (3) Å was present. The reaction of (1) with Co(NO3)2·6H2O and CuCl2·2H2O in methanol afforded the corresponding metal complexes. The obtained solids were further investigated by elemental analysis and UV-Vis titration that confirmed the formation of [CoL] and [ClCuHL] complexes. However, recrystallizaion of the Co(II) complex in dimethylsulfoxide caused the complete hydrolysis of the imine bond and afforded a Co(II) complex in which two 5-nitro-salicylaldehyde and two DMSO molecules were coordinated to the central metal in an octahedral fashion. This structure (2) was also confirmed by single crystal X-ray analysis.

Keywords

Schiff Base, Thiazoline Ligand, Disulfide Bond, Co(II) and Cu(II) Complexes, Hydrolytic Cleavage.
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  • Synthesis, Characterization and Crystal Structure of a New Schiff Base Ligand from a Bis(Thiazoline) Template and Hydrolytic Cleavage of the Imine Bond Induced by a Co(II) Cation

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Authors

Jafar Attar Gharamaleki
Kharazmi University, Tehran, Iran, Islamic Republic of
Fahimeh Akbari
Kharazmi University, Tehran, Iran, Islamic Republic of
Akram Karbalaei
Kharazmi University, Tehran, Iran, Islamic Republic of
Kamran B. Ghiassi
Department of Chemistry, University of California, Davis, CA, United States
Marilyn M. Olmstead
Department of Chemistry, University of California, Davis, CA, United States

Abstract


The reaction of bis-[2-amino-4-pheny1-5-thiazolyl] disulfide with 5-nitro-salicylaldehyde in absolute ethanol resulted in the formation of a new Schiff base ligand H2L (1). Characterization of the ligand was performed by FT-IR, 1H NMR, 13C NMR, UV-Vis, elemental analysis and single crystal X-ray diffraction. The ligand, (1), possesses a disulfide -S-S- bridge of 2.1121 (3) Å length, and the molecule adopts a cis-conformation around this bond. In the crystal structure of (1), an intramolecular O-H···N hydrogen bond with D… A distance of 2.69 (3) Å was present. The reaction of (1) with Co(NO3)2·6H2O and CuCl2·2H2O in methanol afforded the corresponding metal complexes. The obtained solids were further investigated by elemental analysis and UV-Vis titration that confirmed the formation of [CoL] and [ClCuHL] complexes. However, recrystallizaion of the Co(II) complex in dimethylsulfoxide caused the complete hydrolysis of the imine bond and afforded a Co(II) complex in which two 5-nitro-salicylaldehyde and two DMSO molecules were coordinated to the central metal in an octahedral fashion. This structure (2) was also confirmed by single crystal X-ray analysis.

Keywords


Schiff Base, Thiazoline Ligand, Disulfide Bond, Co(II) and Cu(II) Complexes, Hydrolytic Cleavage.