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Spectroscopic, Thermal and Biological Studies on Newly Synthesized Cu(II), Ni(II) and Co(II) Complexes with 3-N-2-hydroxyethylamine Benzanthrone and 3-N-2-aminoethylamine Benzanthrone
Spectroscopic, Thermal and Biological Studies on Newly Synthesized Cu(II), Ni(II) and Co(II) Complexes with 3-N-2-hydroxyethylamine Benzanthrone and 3-N-2-aminoethylamine Benzanthrone
Journal of the Korean Chemical Society. 2011. Feb, 55(1): 28-37
Copyright © 2011, The Korean Chemical Society
  • Received : January 20, 2010
  • Accepted : December 06, 2010
  • Published : February 20, 2011
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About the Authors
Moamen S. Refat
Department of Chemistry, Faculty of Science, Taif University, 888-Taif, Kingdom Saudi Arabia
msrefat@yahoo.com
Adel S. Megahed
Department of Chemistry, Faculty of Science, Taif University, 888-Taif, Kingdom Saudi Arabia
Ibrahim M. El-Deen
Department of Chemistry, Faculty of Science, Port Said University, Port Said, Egypt
Ivo Grabchev
Institute of Polymers, Bulgaria Academy of Science, 1113-Sofia, Bulgaria
Samir El-Ghol
Department of Chemistry, Faculty of Science, Port Said University, Port Said, Egypt

Abstract
Spectroscopic (infrared, electronic and 1 H-NMR), elemental analyses CHN, molar conductivity, thermogravimetric analyses (TGA/DTG) and biological studies, of both benzanthrone derivatives 3-N-2-hydroxy ethylamine benzanthrone (HEAB) and 3-N-2-amino ethylamine benzanthrone (AEAB) with Cu(II), Co(II) and Ni(II) chlorides were discussed herein. Based on the above studies, HEAB ligand was suggested to be coordinated to each metal ions via hydroxo and amino groups to form [Cu(HEAB)(Cl) 2 ].2H 2 O, [Co(HEAB)(Cl) 2 (H 2 O) 2 ].8H 2 O and [Ni(HEAB)(Cl) 2 (H 2 O) 2 ].7H 2 O coordinated complex. On the other hand, AEAB has an octahedral coordinated feature with formulas [Cu(AEAB)(Cl) 2 (H 2 O) 2 ].2H 2 O, [Co(AEAB)(Cl) 2 (H 2 O) 2 ].4H 2 O and [Ni(AEAB)(Cl) 2 (H 2 O) 2 ]. 6H 2 O. The molar conductance values at 25℃ for all complexes in DMF are slightly higher than free ligands; this supported the presence of chloride ions inside the coordination sphere. Both benzanthrone ligands and their complexes have been screened against different kinds of bacteria.
Keywords
INTRODUCTION
Benzanthrone dyes are well know as luminophore dyes emitting in the region from yellow-green to red-purple fluorescence, depending on their structure, 1 their derivatives have a wide variety of applications because of their excellent color characteristics and high photostability. 2 Benzanthrone dyes exhibit, both in solution and in the solid state, bright fluorescence and high photostability and find use as dye light fluorescent. Pigments for synthetic textile materials, 2 due to their bright color, intense fluorescence and good thermostability, are widely used for coloration of polymers. 3
Recent studies have shown that at least some benzanthrone derivatives have a potential for the nontraditional application as components in color liquid crystalline displays of the “guest-host” type. 4 - 7 Benzanthrone derivatives especially (3-nitrobenzanthrone) are the strongest mutagen, 8 metabolic activation of nitroaromatic hydrocarbons occurs through N-reduction to form the N-hydroxyl arylamine, which can bind directly to DNA or undergo further activation by esterification to produce species highly reacting with DNA. 9 - 12
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Structure of benzanthrone derivatives.
On other hand, transition metal complexes play a central role in the construction of molecular materials which display unusual conducting and magnetic properties and find applicability in material chemistry, supramolecules and biochemistry. 13 - 17 A number of reviews 18 - 24 have been published on the general biochemistry of copper, electronic aspects of active sites 25 , 26 and relevant model chemistry of simple copper complexes, 27 , 28 also nickel is one of the most toxic metal among transition metals, it shows the toxicity even in low doses to both plants and animals 29 , 30 in general, first row of transition metal complexes with such ligands have a wide range of biological activities. 31 - 35
With the great important of benzanthrone and their new transition metal complexes, we are discussed in this paper the spectroscopic characterization, thermal and biological activities. The ligands 3-N-2-hydroxy ethylamine benzanthrone (HEAB) and 3-N-2-amino ethylamine benzanthrone (AEAB) are presented in . 1 .
EXPERIMENTAL
CuCl 2 .4H 2 O, CoCl 2 .6H 2 O and NiCl 2 .6H 2 O and the other chemicals were purchased from Fluka and Merck companies, and were used without further purification as received.
- Synthesis of Ligands
Synthesis of 3-alkyl amino benzanthrone dyes derivatives like (HEAB) and (AEAB) was designed in ( 1 ). 3-Nitro benzanthrone is the initial product for the synthesis of new dyes which was prepared by nitration of benzanthrone. 36 The final products were obtained with good yield by nucleophilic substitution of the nitro group in 3-nitro benzanthrone with primary aliphatic amines NH 2 R (where R=CH 2 CH 2 OH; CH 2 CH 2 NH 2 ) in N,N-dimethylformamide(DMF). In this case, the electron-accepting carbonyl group of the benzanthrone molecule favors the nucleophilic substitution reaction of the nitro group with aliphatic amines NH 2 R. The products were characterized by m.p., mass spectra, elemental analysis, IR and 1 H-NMR spectroscopic.
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- Synthesis of complexes
[Cu(HEAB)(Cl)2].2H2O, [Co(HEAB)(Cl)2(H2O)2].8H2O and [Ni(HEAB)(Cl)2 (H2O)2].7H2O: Each of CuCl 2 .2H 2 O (0.845 g, 0.05mol), CoCl 2 .6H 2 O (1.19 g, 0.05mol) or NiCl 2 . 6H 2 O (1.19 g, 0.05 mol) was dissolved in ethanol (20 ml) with gently heated. The metal salt solutions were suspended in (10 ml) ethanol of HEAB (2.91 g, 0.1 mol). The reaction mixtures were refluxed for 4 hours at 80 ℃. The color complexes were precipitated after cooling, filtered off and washed several times with ethanol and dried under vacuo over CaCl 2 .
[Cu(AEAB)(Cl)2(H2O)2].2H2O, [Co(AEAB)(Cl)2(H2O)2]. 4H2O and [Ni(AEAB)(Cl)2 (H2O)2].6H2O: Each of CuCl 2 . 2H 2 O (0.845 g, 0.05 mol), CoCl 2 .6H 2 O (1.19 g, 0.05 mol) or NiCl 2 .6H 2 O (1.19 g, 0.05 mol) was dissolved in ethanol (20 ml) with gently heated. The metal salt solutions were suspended in (10 ml) ethanol of AEAB (2.91 g, 0.1 mol). The reaction mixtures were refluxed for 2 hours at 70 ℃. The color complexes were precipitated after cooling, filtered off and washed several times with ethanol and dried under vacuo over CaCl 2 .
- Analysis
Elemental analyses (C, H, and N) were performed using a Perkin-Elmer CHN 2400 elemental analyzer. The percentage of metal ions was calculated gravimetrically with metal oxides formal. Molar conductance measurements in DMSO solvent at 25 ℃ for the HEAB and AEAB ligands and their complexes with concentration 1.0×10 -3 mol/l were carried out using Jenway 4010 conductivity meter. 1 H-NMR spectra were operated using Varian Gemini 200 MHz spectrometer with DMSO as solvent, chemical shift are given in ppm relative to tetramethylsilane. Electron impact mass spectra were recorded on a Jeol, JMS, DX-303 mass spectrometer. The UV/Vis, spectra were obtained in DMSO solution with concentration of (1.0×10 -3 M) for the (HEAB), (AEAB) ligands and their six complexes with a Jenway 6405 Spectrophotometer using 1 cm quartz cell, in the range of 200-800 nm. Infrared spectra (4000-400 cm -1 ) were recorded as KBr pellets on Bruker FT-IR Spectrophotometer.
Thermogravimetric analyses (TG/DTG) were carried out in the temperature range from 25 to 800 ℃ in a steam of nitrogen atmosphere using Shimadzu TGA 50H thermal analysis. The experimental conditions were: platinum crucible, nitrogen atmosphere with a 30 ml/min flow rate and a heating rate 10 ℃/min.
All the antimicrobial experiments involved with the free ligands and their complexes were carried out according to the filter paper disc method. The investigated isolates of bacteria were seeded in tubes with nutrient broth (NB). The seeded NB (1.0 cm 3 ) was homogenized in the tubes with 9 cm 3 of melted (45 ℃) nutrient agar (NA). The homogeneous suspensions were poured into Petri dishes. The discs of filter paper (diameter 4 mm) were ranged on the cool medium. After cooling on the formed solid medium, 2.0×10 -5 l of the investigated compounds was applied using a micropipette. After incubation for 24 hours in a thermostat at 25-27 ℃, the inhibition (sterile) zone diameters (including disc) were measured and expressed mm. An inhibition zone diameter over 7 mm indicates that the tested compound is active against the bacteria under investigation. The antibacterial activities of the investigated compounds were tested against Escherichia coli , Pseudomonas aeruginosa as (gram negative), Bacillus subtilis and staphylococcus aureus as (gram positive). The concentration of each solution was 1.0×10 -3 mol/l. Commercial DMSO was employed to dissolve the tested samples.
RESULTS AND DISCUSSION
Satisfactory data of both CHN analysis and the percentage of metals used Cu(II), Co(II) and Ni(II) were confirmed the general formula of the benzanthrone complexes as: [Cu(HEAB)(Cl) 2 ]2H 2 O; [M(HEAB)(Cl) 2 (H 2 O) 2 ].XH 2 O (where M=Co(II) or Ni(II); X=7 or 8) and [M(AEAB) (Cl) 2 (H 2 O) 2 ].yH 2 O, (where M=Cu(II); Co(II) or Ni(II) and y=2; 4 or 6). The presence of chloride ions in the inner coordination sphere was tested against silver nitrate. The isolated benzanthrone solid complexes have an amorphous powder and structure and stable in air. The analytical and physical properties of the synthetic complexes are given in 1 .
Elemental analysis and physical data of: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2].7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2].4H2O and (H): [Ni(AEAB) (Cl)2(H2O)2].6H2O
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Elemental analysis and physical data of: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2].7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2].4H2O and (H): [Ni(AEAB) (Cl)2(H2O)2].6H2O
- Mass Spectra
The electron impact mass spectrum of the start material 3-nitrobenzanthrone show the following molecular ions and characteristic fragment ions ( . 2 ). Molecular ion at 275 m/z and base peak at 200 m/z and the other fragments appeared at 150, 174, 189, 217, 229 and 245.
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Electron impact mass spectra of 3-nitrobenzanthrone.
- Molar conductance
The molar conductance (Λ m ) values of benzanthrone and their metal(II) complexes ( 1 ) have been performed using DMSO as solvent at 25 ℃ with concentration of 10 -3 M. The molar conductance of these complexes lies in the range of 39-108 Ω -1 cm -1 mol -1 . These results indicate that the behavior of these complexes is a slightly electrolytic nature comparison with free ligand. According to the mentioned results, we can deduce that the chloride ions were appeared inside the coordination sphere of all complexes and the difference range of molar conductance depends upon the degree of the soluble of each complex. The molar conductance data was agreement with the proposed composition of formed complexes.
- Electronic Spectra
The electron donor-acceptor interaction with 3-substituted benzanthrone occurs between its electron-accepting (carbonyl group) and the electron-donating group in C-3 position of the chromophoric system, 36 the path of the charge-transfer is given on 2 . The spectra of the ligand 3-N-2-hydroxy ethylamine benzanthrone (HEAB) in DMF are shown in . 3 . There are two detected absorption bands at around 233 and 362 nm assigned to π-π * and n-π * , respectively, intraligand transitions. These transitions also found in the spectra of the complexes but they are shifted and increased in the intensity confirming the coordination of the ligand to the metal ions 2 . The spectra of the ligand 3-N-2-amino ethylamine benzanthrone (AEAB) in DMF are shown in . 3 . There are two detected absorption bands at around 232 and 387 nm 2 . Assigned to π-π * and n-π * , respectively, the 3-substituted benzanthrone derivatives exhibited the following disposition of the energetic levels Tπ-π * * * * . 37 , 38
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Electronic spectra of HEAB, AEAB and its nickel complexes.
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Electronic spectra of HEAB, AEAB and their complexes
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Electronic spectra of HEAB, AEAB and their complexes
- Spectroscopic characterization
Infrared Spectrum: 3 includes the most important IR spectral data of 3-N-2-hydroxy ethylamine benzanthrone (HEAB) and 3-N-2-amino ethylamine benzanthrone (AEAB) and their metal complexes. Infrared spectra of the ligand (HEAB), showed two absorption broad bands in the region of 3386 and 3202 cm -1 , which assigned to the stretching vibrations of ν(O-H) and secondary amino group ν(N-H), respectively. The band at 1175 cm -1 assigned to stretching vibration ν(C-N) (imide band) and the absorption band at 1059 cm -1 assigned to stretching vibration ν(C-O). On complexation the position of these bands are shifted toward higher wave number by 8-19 cm -1 and 12-18 cm -1 , respectively, ( . 4 ).
Infrared spectra of: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2]. 7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2].4H2O and (H): [Ni(AEAB)(Cl)2(H2O)2].6H2O
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Infrared spectra of: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2]. 7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2].4H2O and (H): [Ni(AEAB)(Cl)2(H2O)2].6H2O
On the other hand, ligand (AEAB) contain amino group (NH 2 ) and secondary amino group ν(NH) showed absorption broad bands in the region of 3350 cm -1 and 3231 cm -1 , which can be assigned to stretching vibrations ν(NH 2 ) and secondary amino group ν(NH), respectively. The band at 1085 cm -1 and 1174 cm -1 assigned to stretching vibration ν(C-N) of NH 2 and ν(C-N) of NH, respectively. After complex formation the position of stretching vibrations of (NH 2 ) and secondary amino group (NH) are shifted toward higher wavenumber by 10-17 cm -1 and 14-18 cm -1 , respectively. The band of stretching vibration ν(C-N) of (NH 2 ) and stretching vibration ν(C-N) of (NH) are shifted toward lower wavenumber by ~17 cm -1 and ~5 cm -1 , respectively.
Infrared spectra of complexes exhibited broad bands at 3430-3440 cm -1 that are attributed to ν(OH) of the crystal water molecules. While the bands observed at approximately 878 cm -1 are assigned to coordinated water molecules. 39 Bands in the region ~550 and ~420 may be assigned to ν(M-N) and ν(M-O), respectively. 40 This result indicates that the coordination takes place through the nitrogen and oxygen atoms of NH and OH groups in 3-N-2-hydroxy ethylamine benzanthrone (HEAB) and through both of nitrogen atoms of NH 2 and NH groups in 3-N-2-amino ethylamine benzanthrone (AEAB) . 4 .
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Infrared spectra of: A=HEAB; B=[Cu(HEAB)(Cl)2]. 2H2O; C=[Co(HEAB)(Cl)2 (H2O)2].8H2O; D=[Ni(HEAB)(Cl)2(H2O)2]. 7H2O E=AEAB; F=[Cu(AEAB)(Cl)2(H2O)2].2H2O; G=[Co(AEAB) (Cl)2(H2O)2].4H2O; H=[Ni(AEAB)(Cl)2(H2O)2].6H2O.
1H-NMR Spectrum: The chemical shift (δ, ppm) of the proton magnetic resonance of both HEAB and AEAB have been recorded as follows:
1 HNMR (DMSO-d 6 at 200MHZ):
( HEAB ): δ: 2.43(s,1-H):OH; 3.54(t.2H):NCH 2 ; 3.72(t,2H): OCH 2 ; 4.16(s, 1-H): NH; 6.66(d,1H,J=8.0 HZ):2-H; 7.26 (m,1H): 5-H, 8-H and 10-H; 7.80(m, 2H): 4-H and 9-H; 8.24(m, 2H): 6-H and 7-H: 8.56(d, 1H, J=8.0 HZ): 1-H. 41
( AEAB ): δ=2.54(t,2-H):NH 2 ; 3.42(t.2H)NCH 2 ; 3.30(t,2H): (NH 2 )CH 2 ; 3.40(s, 1-H): NH; 6.89(d,1H,J=8.0 HZ): 2-H; 7.85(m,1H): 5-H, 8-H and 10-H; 8.17(m, 2H): 4-H and 9-H; 8.40(m, 2H): 6-H and 7-H: 8.62(d, 1H, J=8.0 HZ): 1-H.
- Thermal Studies
The thermal degradation of all complexes was studied using thermogravimetric techniques and a temperature range of 25-800 ℃ ( . 5 ). The thermal stability data are listed in 4 . The data from thermogravimetric analysis clearly indicated that the decomposition of the complexes proceeds in three or four steps. Crystal water molecules were lost in between 25-150 ℃ and chloride ions or coordinated water molecules were lost in between 200-350 ℃. Metal oxides were formed above 600 ℃ for the Cu(II), Co(II) and Ni(II) complexes. The thermal analysis of ligands 3-N-2-hydroxy ethylamine benzanthrone (HEAB) and 3-N-2-amino ethylamine benzanthrone (AEAB) melts at 216 and 254 ℃, respectively, with simultaneous decomposition. The main degradation peaks were observed at 314 and 334 ℃ in the TG profile. From the TG profile of (HEAB) and (AEAB), it appears that the sample decomposes in one sharp stage over the wide temperature range 25-800 ℃. The decomposition occurs with a mass loss of 62.81% and its calculated value is 63.01% for (HEAB) ligand and mass loss of 47.23% and its calculated value is 46.70% for (AEAB) ligand.
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TGA diagrams of HEAB, AEAB ligands and their metal complexes.
Thermo gravimetric data of: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2]. 7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2].4H2O and (H): [Ni(AEAB)(Cl)2(H2O)2].6H2O
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Thermo gravimetric data of: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2]. 7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2].4H2O and (H): [Ni(AEAB)(Cl)2(H2O)2].6H2O
The thermal analysis of the chelates under study evinces the following weight losses 7.11-20.89% loss of water molecules of hydration over the rang 25-120 ℃ interval
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The thermal decomposition stages of benzanthrone complexes.
(calculated 7.24-21.56%) for the Cu(II), Co(II) and Ni(II) complexes.
  • • 3.10-7.01% loss of water molecules of coordination over the range 120-360 ℃ interval (calculated 3.40-6.36%) for Co(II) and Ni(II) complexes.
  • • 27.28-48.745 elimination of Cl2molecules and organic moiety over the rang 120-380 ℃ interval (calculated 21.52-49.56%) for Cu(II) complexes.
  • • 18.37-57.64% elimination of Cl2molecules and organic moiety over the temperature rang 200-600 ℃ interval (calculated 17.77-58.98%) for the Co(II) and Ni(II) complexes.
  • • 16.04-27.67% residues of metal oxides remain over 600-800 ℃ interval (calculated 16.95-27.94%) for Cu(II), Co(II) and Ni(II) complexes.
In general, the stages of thermal decomposition of the complexes can be written as 3 .
- Kinetic studies
In recent years, there has been increasing interest in determining the rate-dependent parameters of solid-state non-isothermal decomposition reactions by analysis of TG curves. Several equations 42 - 49 have been proposed as means of analyzing a TG curve and obtaining values for kinetic parameters. Many authors 42 - 46 have discussed the advantages of this method over the conventional isothermal method.
Kinetic Parameters using the Coats-Redfern(CR) and Horowitz-Metzger (HM)) for: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2].7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2]. 4H2O and (H): [Ni(AEAB)(Cl)2(H2O)2].6H2O
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Kinetic Parameters using the Coats-Redfern(CR) and Horowitz-Metzger (HM)) for: (A): HEAB, (B): [Cu(HEAB)(Cl)2].2H2O, (C): [Co(HEAB)(Cl)2(H2O)2].8H2O, (D): [Ni(HEAB)(Cl)2(H2O)2].7H2O, (E): AEAB, (F): [Cu(AEAB)(Cl)2(H2O)2].2H2O, (G): [Co(AEAB)(Cl)2(H2O)2]. 4H2O and (H): [Ni(AEAB)(Cl)2(H2O)2].6H2O
Most commonly used methods for this purpose are the differential method of Freeman and Carroll 42 integral method of Coat and Redfern, 44 the approximation method of Horowitz and Metzger. 47 In the present investigation, the general thermal behaviors of the complexes in terms of stability ranges, peak temperatures and values of kinetic parameters are listed in 5 . The kinetic parameters have been evaluated using the mentioned methods and the results obtained by these methods are well agreement with each other.
The entropy of activation, Δ S * , enthalpy activation, Δ H * , and Gibbs free energy, Δ G * , were calculated from; Δ H * = E * - RT and Δ G * = Δ H * - T Δ S * , respectively.
From the kinetic and thermodynamic data resulted from the TGA curves and tabulated in 5 , the following outcome can be discussed as follows:
  • 1. The thermodynamic data obtained with the two methods are in harmony with each other.
  • 2. The higher values of activation energies of the both HEAB and AEAB benzanthrone complexes led to thermal stability of the studied complexes.
  • 3. The activation energy of Cu+2and Ni+2complexes is expected to increase in relation with decrease in their radii. The smaller size of the ions permits a closer approach of the ligand. Hence, the E value in the first stage for the Ni+2complex is higher than that for the other Cu+2and Co+2complexes.
  • 4. The correlation coefficients of the Arrhenius plots of the thermal decomposition steps were found to lie in the range 0.9820 to 0.9996, showing a good fit with linear function.
It is clear that the thermal decomposition process of all benzanthrone complexes is non-spontaneous, i.e., the complexes are thermally stable.
- Microbiological investigation
The results of antibacterial actives in vitro of the ligand and all their complexes are represented in 6 . From the results we can see that all the test compounds have a high activity as antibacterial against gram positive ( Bacillus subtili, staphylococcus aureus ) and also toward gram negative ( Escherichia coli , Pseudomonas aeruginosa ).
Antibacterial activity data of the benzanthrone ligands and their metal complexes, inhibition zone(mm)
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Antibacterial activity data of the benzanthrone ligands and their metal complexes, inhibition zone(mm)
The sequence of the antibacterial activity of the Cu(II), Co(II) and Ni(II) benzanthrone complexes can be designed as follows according to the kind of bacteria:
  • i.Bacillus subtili: Co/AEAB>HEAB=Co/HEAB=Ni/HEAB=AEAB=Ni/AEAB>Cu/HEAB=Cu/AEAB
  • ii.staphylococcus aureus: Co/HEAB>HEAB=Ni/HEAB=AEAB>Cu/HEAB>Co/AEAB>Ni/AEAB>Cu/AEAB
  • iii.Escherichia coli: Co/AEAB>Co/HEAB=Ni/AEAB>HEAB=Ni/HEAB=AEAB>Cu/HEAB=Cu/AEAB
  • iv.Pseudomonas aeruginosa: HEAB=AEAB=Co/AEAB=Ni/AEAB>Co/HEAB=Ni/HEAB>Cu/HEAB>Cu/AEAB
Generally, The Co(II) benzanthrone complexes have a higher antibacterial activity than other Cu(II) and Co(II) benzanthrone complexes.
- Structure of the benzanthrone complexes
Finally on the basis of the above studies; the suggested structures of the Cu(II), Co(II) and Ni(II) benzanthrone complexes can be represented in . 6 .
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Suggested structures of the Cu(II), Co(II) and Ni(II) benzanthrone complexes.
CONCLUSION
In conclusion, we have synthesized and characterized six mononuclear Cu(II), Co(II) and Ni(II) complexes of both benzanthrone derivatives 3-N-2-hydroxy ethylamine benzanthrone (HEAB) and 3-N-2-amino ethylamine benzanthrone (AEAB). The complexes have been screened for antibacterial activity against four bacteria. All complexes were discussed using infrared, electronic, 1H-NMR, elemental analyses CHN, molar conductivity and thermogravimetric TGA/DTG investigations.
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