Synthesis, Characterisation, Thermal Properties and Biological Activity of Mannich-Bases (HL And HL1) and HL Complexes with Zn(II) and Cd(II)

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Enaam Ismail Yousif, Nihad Kadhum Hasan, Mohamad J. Al-Jeboori, Baraa Kasim Mohammed

Abstract

The preparation and characterisation of two new Mannich bases; (i) (R)-2-((4-(dimethylamino)phenyl)((2-nitrophenyl)amino)methyl)-5,5-dimethylcyclohexane-1,3-dione (HL) and (ii)4-(tert-butyl)-2-((S)-(phenylamino)(p-tolyl)methyl)cyclohexan-1-one (HL1) are reported. The formation of these compounds was based on a one-pot reaction using CaCl2 as a catalyst. The mixing of 5,5-dimethylcyclohexane-1,3-dione, 4-dimethylaminobenzaldehyde and 2-nitroaniline in an equivalent mole ratio resulted in the synthesis of HL. Meanwhile, the reaction of p-methyl benzaldehyde, 4-(tert-butyl)cyclohexan-1-one and aniline in an equivalent mole ratio gave HL1. More, the complexationbehaviour betweenHLwithZn(II) and Cd(II) chloridesisalso included. The reaction of HL with Zn(II) and Cd(II) metal ions in a 2:1 (L:M) mole ratio resulted in the isolation of homolepticcomplexes, in which the ligand behaves as a tridentate species. The prepared compounds were characterised using a range of analytical and spectroscopic techniques. The characterisation data of HL complexes indicated the isolation of six-coordinate homolepticcomplexes with the general formula; [M(HL)2] (where M= Zn(II) and Cd(II)). The thermal stability of the HL and Cd(II)complex was also investigated. The antibacterial and antifungal activities ofHL and its complexes were examined. The obtained data indicated the complexes are more active against tested organisms, under survey, compared with the free ligand. 

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