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1.
Article in English | MEDLINE | ID: mdl-25988819

ABSTRACT

Two imine compounds, 4-[(E)-(2-methoxybenzylidene)amino]phenol (L(1)) and 4-[(E)-(3,4-dimethoxybenzylidene)amino]phenol (L(2)) were synthesized and characterized by the analytical and spectroscopic methods. The electrochemical and photoluminescence properties of the imine compounds L(1) and L(2) were investigated in different solvents. The compounds L(1) and L(2) show different redox processes at some potentials. The molecular structures of two Schiff base compounds are broadly similar, differing principally in the position, the number of methoxy (-OCH3) groups and dihedral angles between aromatic rings. While the compound L(1) has only one methoxy group located on the o-position with respect to the imine bond (C=N), the L(2) contains two methoxy groups on the p-m-positions with respect to the imine bond. The imine compounds show two or three emission bands in the 619-832 nm range in organic solvents. In the 1.0×10(-3) M concentration, the compounds have the highest excitation and emission bands. The imine compounds L(1) and L(2) were screened for their in vitro cytotoxicity on HeLa cell lines using the xCELLigence system (Real Time Cell Analyzer).


Subject(s)
Antineoplastic Agents/pharmacology , Electrochemical Techniques/methods , Imines/chemistry , Imines/pharmacology , Luminescence , Crystallography, X-Ray , HeLa Cells , Humans , Hydrogen Bonding , Molecular Conformation , Proton Magnetic Resonance Spectroscopy , Solvents , Spectrophotometry, Ultraviolet , Stereoisomerism
2.
Article in English | MEDLINE | ID: mdl-25698438

ABSTRACT

A polymeric potassium complex of p-nitrophenol was synthesized and characterized by analytical and spectroscopic techniques. Molecular structure of the complex was determined by single crystal X-ray diffraction study. X-ray structural data show that crystals contain polymeric K(+) complex of p-nitrophenol. Asymmetric unit consists of one p-nitrophenolate, one K(+) ion and one water molecule. All bond lengths and angles in the phenyl rings have normal Csp2-Csp2 values and are in the expected ranges. The p-nitrophenolate is close to planar with small distortions by some atoms. Each potassium ion in the polymeric structure is identical and eight-coordinate, bonded to four nitro, two phenolate oxygen atoms from five p-nitrophenolate ligands and two oxygen atoms from two water molecules. Electronic, electrochemical, photoluminescence and thermal properties of the complex were also investigated.


Subject(s)
Coordination Complexes/chemistry , Nitrophenols/chemistry , Polymers/chemistry , Potassium/chemistry , Crystallography, X-Ray , Electrochemical Techniques , Luminescence , Models, Molecular
3.
Spectrochim Acta A Mol Biomol Spectrosc ; 136 Pt C: 1388-94, 2015 Feb 05.
Article in English | MEDLINE | ID: mdl-25459697

ABSTRACT

A novel Schiff base ligand was synthesized by the condensation reaction of 2,6-diformylpyridine and 4-aminoantipyrine in MeOH and characterised by its melting point, elemental analysis, FT-IR, (1)H, (13)C NMR and mass spectroscopic studies. Molecular structure of the ligand was determined by single crystal X-ray diffraction technique. The electrochemical properties of the Schiff base ligand were studied in different solvents at various scan rates. Sensor ability of the Schiff base ligand was investigated by colorimetric and fluorometric methods. Visual colour change of the ligand was investigated in MeOH solvent in presence of various metal ions Na(+), Mg(2+), Al(3+), K(+), Cr(3+), Mn(2+), Fe(3+), Co(2+), Ni(2+), Cu(2+), Zn(2+), Cd(2+), Hg(2+) and Pb(2+). Upon addition of Al(3+) ion into a MeOH solution of the ligand, an orange colour developed which is detectable by naked eye. Fluorescence emission studies showed that the ligand showed single emission band at 630-665nm upon excitation at 560nm. Addition of metal ions Na(+), Mg(2+), K(+), Cr(3+), Mn(2+), Fe(3+), Co(2+), Ni(2+), Cu(2+), Zn(2+), Cd(2+), Hg(2+) and Pb(2+) (1:1M ratio) cause fluorescence quenching, however addition of Al(+3) resulted in an increase in fluorescence intensity. No significant variation was observed in the fluorescence intensity caused by Al(3+) in presence of other metal ions. Therefore, the Schiff base ligand can be used for selective detection of Al(3+) ions in the presence of the other metal ions studied.

4.
Spectrochim Acta A Mol Biomol Spectrosc ; 137: 477-85, 2015 Feb 25.
Article in English | MEDLINE | ID: mdl-25238187

ABSTRACT

Two Schiff base compounds, N,N'-bis(2-methoxy phenylidene)-1,5-diamino naphthalene (L(1)) and N,N'-bis(3,4,5-trimethoxy phenylidene)-1,5-diamino naphthalene (L(2)) were synthesized and characterized by the analytical and spectroscopic methods. The electrochemical and photoluminescence properties of the Schiff bases were investigated in the different conditions. The compounds L(1) and L(2) show the reversible redox processes at some potentials. The sensor properties of the Schiff bases were examined and color changes were observed upon addition of the metal cations, such as Hg(II), Cu(II), Co(II) and Al(III). The Schiff base compounds show the bathochromic shift from 545 to 585 nm. The single crystals of the compounds (L(1)) and (L(2)) were obtained from the methanol solution and characterized structurally by the X-ray crystallography technique. The molecule L(2) is centrosymmetric whereas the L(1) has no crystallographically imposed molecular symmetry. However, the molecular structures for these compounds are quite similar, differing principally in the conformation about methoxy groups and the dihedral angle between the two aromatic rings and diamine naphthalene.


Subject(s)
1-Naphthylamine/analogs & derivatives , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Schiff Bases/chemistry , Schiff Bases/pharmacology , 1-Naphthylamine/chemical synthesis , 1-Naphthylamine/chemistry , 1-Naphthylamine/pharmacology , Animals , Antineoplastic Agents/chemical synthesis , Cell Proliferation/drug effects , Chlorocebus aethiops , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Electrochemical Techniques , HeLa Cells/drug effects , Humans , Luminescence , Metals/chemistry , Molecular Structure , Oxidation-Reduction , Photochemical Processes , Schiff Bases/chemical synthesis , Solvents/chemistry , Vero Cells/drug effects
5.
Article in English | MEDLINE | ID: mdl-22571942

ABSTRACT

Three Schiff base ligands (H(2)L(1)-H(2)L(3)) with N(2)O(2) donor sites were synthesized by condensation of 1,5-diaminonapthalene with benzaldehyde derivatives. A series of Cu(II), Co(II), Ni(II), Mn(II) and Cr(III) complexes were prepared and characterized by spectroscopic and analytical methods. Thermal, electrochemical and alkane oxidation reactions of the ligands and their metal complexes were investigated. Extensive application of 1D ((1)H, (13)C NMR) and 2D (COSY, HETCOR, HMBC and TOSCY) NMR techniques were used to characterize the structures of the ligands and establish the (1)H and (13)C resonance assignments of the three ligands. Ligands H(2)L(1) and H(2)L(3) were obtained as single crystals from THF solution and characterized by X-ray diffraction. Both molecules are centrosymmetric and asymmetric unit contains one half of the molecule. Catalytic alkane oxidation reactions with the transition metal complexes investigated using cyclohexane and cyclooctane as substrates. The Cu(II) and Cr(III) complexes showed good catalytic activity in the oxidation of cyclohexane and cyclooctane to desired oxidized products. Electrochemical and thermal properties of the compounds were also investigated.


Subject(s)
Alkanes/chemistry , Coordination Complexes/chemistry , Coordination Complexes/chemical synthesis , Electrochemical Techniques/methods , Schiff Bases/chemistry , Schiff Bases/chemical synthesis , Temperature , Absorption , Catalysis , Crystallography, X-Ray , Cyclohexanes/chemistry , Cyclooctanes/chemistry , Electrons , Hydrogen Bonding , Hydrogen Peroxide/chemistry , Hydrogen-Ion Concentration , Ligands , Magnetic Resonance Spectroscopy , Microwaves , Molecular Conformation , Oxidation-Reduction , Spectrophotometry, Infrared
6.
Spectrochim Acta A Mol Biomol Spectrosc ; 81(1): 184-98, 2011 Oct 15.
Article in English | MEDLINE | ID: mdl-21752697

ABSTRACT

In this study, two Schiff base ligands (HL(1) and HL(2)) and their Cu(II), Co(II), Ni(II), Pd(II) and Ru(III) metal complexes were synthesized and characterized by the analytical and spectroscopic methods. Alkane oxidation activities of the metal complexes were studied on cyclohexane as substrate. The ligands and their metal complexes were evaluated for their antimicrobial activity against Corynebacterium xerosis, Bacillus brevis, Bacillus megaterium, Bacillus cereus, Mycobacterium smegmatis, Staphylococcus aureus, Micrococcus luteus and Enterococcus faecalis (as gram-positive bacteria) and Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli, Yersinia enterocolitica, Klebsiella fragilis, Saccharomyces cerevisiae, and Candida albicans (as gram-negative bacteria). The antioxidant properties of the Schiff base ligands were evaluated in a series of in vitro tests: 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and reducing power activity of superoxide anion radical generated non-enzymatic systems. Electrochemical and thermal properties of the compounds were investigated.


Subject(s)
Alkanes/metabolism , Antioxidants/pharmacology , Coordination Complexes/pharmacology , Schiff Bases/pharmacology , Anti-Infective Agents/analysis , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Antioxidants/analysis , Antioxidants/chemistry , Coordination Complexes/analysis , Coordination Complexes/chemistry , Differential Thermal Analysis , Electrochemistry , Gram-Negative Bacteria/drug effects , Gram-Negative Bacteria/growth & development , Gram-Positive Bacteria/drug effects , Gram-Positive Bacteria/growth & development , Humans , Ligands , Microbial Sensitivity Tests , Models, Biological , Molecular Structure , Oxidation-Reduction/drug effects , Schiff Bases/analysis , Schiff Bases/chemistry , Structure-Activity Relationship
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