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Mixed Ligand, Palladium(II) and Platinum(II) Complexes of Tertiary Diphosphines with S-1H Benzo[D] Imidazole-2-Yl Benzothioate

Karwan Omer Ali1, Hikmat Ali Mohammad2, Thomas Gerber3 and Eric Hosten4

1College of Education and Human Sciences, university of Halabja, Halabja.

2Department of Chemistry, college of Education, university of Salahaddin, Erbil.

3Department of Chemistry, Faculty of Science, Nelson Mandela Metropolitan University, Port Elizabeth, 6031, South Africa Chemistry Department.

4Department of Chemistry, Faculty of Science, Nelson Mandela Metropolitan University, Chemistry Department.

Corresponding Author E-mail: karwang1987@gmail.com

DOI : http://dx.doi.org/10.13005/ojc /330205

ABSTRACT:

Palladium(II) and platinum(II) complexes containing the mixed ligands tertiary diphosphines dppm. dppp and dppf with Thioester ligand S-1H benzo[d] imidazole-2-yl benzothioate (HSBIBT) have been prepared by the reaction of PdCl2 and PtCl2 with one equiv of tertiary diphosphines ligands to form [Pd(k2-dppf)Cl2], [Pd(k2-dppp)Cl2] and [Pt(k2-dppmCl)Cl2] complexes and then add the ligand HSBIBT to these complexes to form mixed ligand complexes. The prepared complexes have been characterized by single-crystal X-ray diffraction, elemental analysis, magnetic susceptibility, molar conductance, IR spectral data and UV-Visible. The results suggested that the ligand HSBIBT bonded to the metal through N atom and square planner geometries were assigned for the complexes.

KEYWORDS:

Palladium. Platinum; Tertiarydiphosphine; Thioester ligand complexes

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Ali K. O, Mohammad H. A, Gerber T, Hosten E. Mixed Ligand, Palladium(II) and Platinum(II) Complexes of Tertiary Diphosphines with S-1H Benzo[D] Imidazole-2-Yl Benzothioate. Orient J Chem 2017;33(2).


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Ali K. O, Mohammad H. A, Gerber T, Hosten E. Mixed Ligand, Palladium(II) and Platinum(II) Complexes of Tertiary Diphosphines with S-1H Benzo[D] Imidazole-2-Yl Benzothioate. Orient J Chem 2017;33(2). Available from: http://www.orientjchem.org/?p=32034


Introduction

Benzimidazole is the heterocyclic aromatic organic compound1. This bicyclic ring system consist of benzene ring joined with 4- and 5- situation of imidazole ring, imidazole ring having non adjacent two nitrogen atoms2. 2-Mercaptobenzimidazole derived from benzimidazole with thiol group in the 2-position. It holds extra chemical names such as, o-phenylen thiourea, benzimidazol-2-thion with formula of C7H6N2S3,4. In 2-mercaptobenzimidazole have two N atoms and one S atom and they can independently contribute to its binding to metal5. 2-mercaptobenzimidazole derivatives, one of the most important derivatives of benzimidazole exhibited a wide range of importance biological activities such as antimicrobial6, antihistamine7, neutropic8 and analgesic9, antiprotozoal, antiviral, and anticancer activities10. Metal derivatives of heterocyclic-2-thiones have shown a variety of biochemical application: as antidandruff, antifungal, antibacterial, antibiotic and in shampoos, hair creams, plant diseases and hepatitis11.

Thioesters are important class of organosulfur compounds that play a major role in the construction of pharmaceutical, biological, industrial and natural products. In this respect, thioesters synthesis is one of the most important tasks in organosulfur chemistry. The esterification of thiols is the best and most common strategy for the synthesis of Thioesters12. Diphosphines are a class of chelating ligands that contain two phosphine groups connected by a bridge (also referred to as a backbone). The bridge, for instance, might consist of one or more methylene groups or multiple aromatic rings with heteroatoms attached13. The structure of the backbone and the substituents attached to the phosphorus atoms influence the chemical reactivity of the diphosphine ligand in metal complexes through steric and electronic effects13. Phosphorus ligands typically bind to the metal centers via the lone pair of electrons on the phosphorus14.

Experimental

Materials and Instrumentation

The compounds PtCl2, PdCl2, dppm, dppp, dppf and S-1H benzo[d] imidazole-2-yl benzothioate (HSBIBT) were commercially available and obtained from Yacoo chem. China. The complexes [Pd(k2-dppf)(HSBIBT)Cl]Cl, [Pd(k2-dppp) (HSBIBT)Cl]Cl, [Pt(k2-dppm) (HSBIBT)Cl]Cl were prepared according to the literature.

Elemental CHNS analysis were carried out on a EuroEA 3000 instrument. The FT-IR spectra in range (4000-200 cm-1) were recorded as CsI disc on Shimadzu IRAffinity-1S FTIR Spectrophotometer, and FT-IR spectra in range (4000-400 cm-1) were recorded as KBr disc on Shimadzu, FT-IR spectroscopy Mod IR Affinity-1CE spectrophotometer. UV-Visible spectra were measured using AE-UV1609 (UK) CO., LTD Shimadzu, in the range (200-800) nm. The magnetic susceptibility values of the prepared complexes were carried out at room temperature using Bruker Magnet BM6. Conductivity measurements were made on a conductivity meter type Senz µSiemen tester 4200 (093 cell constant) (UK.). Melting points were measured on Melting Point-MPD-100 Pixel Technology CO., Limited apparatus.

Synthesis of [Pd(k2-dppf)Cl2].CH2Cl2

The solution of dppf (1.6632g, 3mmol) in 15ml CH2Cl2 was added to a solution of PdCl2 (0.5320g, 3mmol) that dissolved in 2 cm3 ethanol and 2 cm3 concentrate HCl. The mixture was reflux for 3 hrs. And then the solvent was evaporate at room temperature to give red precipitate. A small portion of this complex was dissolve in CH2Cl2 and set to slow evaporation at room temperature after a few days, the red colored needle crystals were formed suitable for single-crystal diffraction analysis15. The melting point is 253°C, yield is 2.086gm (95%), formula: [Pd(k2-dppf)Cl2] and  M.wt.is 816.58 gm/mole, as shown in Figure 1.

Synthesis of [Pd(k2-dppf)(HSBIBT)Cl]Cl

A solution of ligand (0.0509 g, 0.2 mmol) in CH2Cl2 (15 cm3) was added to a solution of [Pd(k2-dppf)Cl2] (0.1463 g, 0.2 mmol) in CH2Cl2 (15cm3), and the mixture was heated under reflux for 4 hrs and then the Solvent was evaporated at room temperature to give a red solid. Yield= 91 %, m.p= 139-141°C. as shown in Figure 1.

Synthesis of [Pd(k2-dppp)Cl2]

The solution of dppp (1.2373g, 3mmol) in 15ml CH2Cl2 was added to a solution of PdCl2 (0.5320g, 3mmol) that dissolved in 2 cm3 ethanol and 2cm3 concentrate HCl. The mixture was reflux for 3 hrs. And then the solvent was evaporate at room temperature to give pale yellow precipitate. A small portion of this complex was dissolve in CH2Cl2 and set to slow evaporation at room temperature after a one week, the yellow colored needle crystals were formed suitable for single-crystal diffraction analysis15. The Melting point is 277 °C, yield is 1.664gm (94%), formula: [Pd(k2-dppp)Cl2] and M.wt.is 589.72 gm/mole. as shown in Figure 1.

Synthesis of [Pd(k2-dppp)(HSBIBT)Cl]Cl

A solution of ligand (0.0509 g, 0.2 mmol) in CH2Cl2 (15 cm3) was added to a solution of [Pd(k2-dppp)Cl2] (0.1179 g, 0.2 mmol) in CH2Cl2 (15cm3), and the mixture was heated under reflux for 4 hrs and then the Solvent was evaporated at room temperature to give a yellow solid. Yield= 93 %, m.p= 142-144°C. as shown in Figure 1.

Synthesis of [Pt(k2-dppmCl)Cl2]

The solution of dppm (1.1532g, 3mmol) in 15ml CH2Cl2 was added to a solution of PtCl2 (0.7979g, 3mmol) that dissolved in 2 cm3 ethanol and 2cm3 concentrate HCl. The mixture was reflux for 3 hrs. And then the solvent was evaporate at room temperature to give yellow precipitate. A small portion of this complex was dissolve in CH2Cl2 and set to slow evaporation at room temperature after a one week, the yellow colored needle crystals were formed suitable for single-crystal diffraction analysis15. The melting point is  ˃ 300°C, yield is 1.756gm (90%), formula: [Pt(k2-dppmCl)Cl2] and M.wt.is 667.43 gm/mole. as shown in Figure 1.

Synthesis of [Pt(k2-dppmCl)(HSBIBT)Cl]Cl

A solution of ligand (0.0509 g, 0.2 mmol) in CH2Cl2 (15 cm3) was added to a solution of [Pt(k2-dppmCl)Cl2] (0.1300 g, 0.2 mmol) in CH2Cl2 (15cm3), and the mixture was heated under reflux for 4 hrs and then the Solvent was evaporated at room temperature to give a yellow solid. Yield= 90 %, m.p= 117-119°C. as shown in Figure 1.

Figure 1: synthesis route of complexes

Figure 1: synthesis route of complexes



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X-ray Crystallography

Single crystal X-ray crystallography studies were performed at 200 k using a Bruker Kappa Apex II diffractometer with graphite monochromated Mo Kα radiation (λ = 0.71073 °A). For data collection, Apex-II was used while for cell refinement and data reduction, SAINT was used16. The structures were solved by direct methods applying SHELXL-201317, with SHELXLE18 as a graphical interface.

Red crystals of 1, yellow crystals of 3 and yellow crystals of 5 suitable for X-ray crystallographic measurements were obtained by slow evaporation of dichloromethane solutions of the respective complex. Table 4 gives the crystallographic data and collection parameters. All Non-hydrogen atoms were refined with anisotropic displacement parameters. Hydrogen atoms were included in the models by calculating the positions (riding model) and refined with calculated isotropic displacement parameters.

Results and Discussion

The mixed ligand complexes were synthesized by two steps. The first step include the preparation of metal complexes with tertiary diphosphines ligands [MCl2(k2-PPh2(CH2)nPPh2)] where n= 1,3 with [MCl2(k2-dppf)], and M= Pd and Pt. The second step include the synthesis of mixed ligand complexes by addition of S-1H-benzo[d]imidazole-2-yl benzothioate (HSBIBT) ligand to tertiary diphosphines metal complexes. The physical data of complexes are given in Table (1), the suggested molecular formula are supported by IR spectra, UV-Visible sepectra, elemental analysis, magnetic moment and conductivity measurement.

Table 1: physical characteristics and analytical data for metal complexes

Complex Color Yield % M.P °C

Elemental analysis, calc. (found) %

C H N S
[Pd(k2-dppf)(HSBIBT)Cl]Cl Red 91 142-144 58.47(58.47) 3.84(3.75) 2.75(2.84) 3.15(3.24)
[Pd(k2-dppp)(HSBIBT)Cl]Cl Yellow 93 139-141 58.45(58.35) 4.18(4.15) 3.26(3.32) 3.46(3.79)
[Pt(k2-dppmCl)(HSBIBT)Cl]Cl Yellow 90 117-119 51.46(51.78) 3.60(3.43) 2.93(3.09) 3.44(3.54)

 

IR Spectral Studies

The infrared spectrum of free (HSBIBT) ligand is characterized by intense absorption band at 1712 cm-1. This band is assigned to ν(C=O) group19, 4. The stretching frequency of ν(C=N) band which appeared at 1618 cm-1 forfree (HSBIBT) ligand. This band was shifted to lower frequency during complexation due to the coordination of nitrogen atom to the metals20 (Table 2).

The infrared spectra of complexes showed medium intensity bands in the range 513 to 570 cm-1, these bands are attributed to ν(M-N)21. Also showed a bands in the range 370 to 391cm-1, these bands are related to ν(M-Cl)22. Further support for the coordinated phosphines ligands has been provided by the appearance of new bands in the range 285 to 291cm-1, these bands are assigned to ν(M-P)23.

Magnetic Moments

The magnetic moments of complexes [Pd(k2-dppf)(HSBIBT)Cl]Cl (2), [Pd(k2-dppp)(HSBIBT)Cl]Cl  (4) and [Pt(k2-dppmCl)(HSBIBT)Cl]Cl  (6)  are 0.54, 0.6 and 0.44 B.M. respectively (Table 3), suggesting a square planer  arrangement around the metal and complexes are diamagnetic24,25.

Electronic Spectral Studies

The UV-Vis spectrum in 10-3 M chloroform (Table 3) shows three absorption bands of Pd(II) complex (2), at 20661 cm-1, 28571 cm-1, and 33783 cm-1 which are assigned to the 1A1g→ 1A2g , 1A1g→ 1Eg  and charge transfer transition respectively, these bands are reasonable to square planner geometry26. The UV-visible spectrum of Pd(II) complex(4), gave three spins allowed transitions at 24038 cm-1, 29411 cm-1, and 32679  cm-1 which are assigned to the 1A1g1A2g , 1A1g→ 1Eg and charge transfer transition respectively. The UV-visible spectrum of Pt(II) complex(6), shows three absorption bands at 23923 cm-1, 27777 cm-1, and 32573 cm-1 which are  assigned to the 1A1g1A2g , 1A1g1Eg and charge transfer transition respectively, These transitions value are indicated to square planner geometry27.

Conductivity Measurement

The molar conductivity of complexes [Pd(k2-dppf)(HSBIBT)Cl]Cl (2), [Pd(k2-dppp)(HSBIBT)Cl]Cl  (4) and [Pt(k2-dppmCl)(HSBIBT)Cl]Cl  (6) in dimethyl sulfoxide (DMSO) are 34.2, 41.4 and 36 (cm2.ohm-1. mol-1) (Table 3) suggesting that they are electrolytes complexes28,29.

Table 2: IR frequencies (cm-1) of the compounds 

complex ν(N-H)   ν(C=O)   ν(C=N)   ν(P-Ph)   ν(P-C)   ν(M-N)   ν(M-P)   ν(M-Cl)  
HSBIBT 3151 1712 1618 - - - - -
2 3165 1712 1608 1435 - 513 285 370
4 3159 1712 1612 1435 513 540 288 383
6 3153 1712 1608 1436 509 559 291 391

 

Table 3: Electronic spectra, magnetic moments and molar conductivity of complexes

complex λmax(nm)/ Chloroform assignments µeff (BM)a ɅM-1cm2 mol-1)/ DMSO
2 484350296 1A1g→ 1A2g1A1g→ 1EgC.T 0.54 34.2
4 416340306 1A1g→ 1B1g1A1g→ 1EgC.T 0.6 41.4
6 418360307 1A1g→ 1A2g1A1g→ 1EgC.T 0.44 36

 

X-ray Crystal Structures

The [Pd(k2-dppf)Cl2].CH2Cl2 complex was crystallized in a dichorometahne (CH2Cl2) at room temperature. After one week, the red colored needle type crystals had grown from the CH2Cl2 solvent and these crystals were subjected to single-crystal X-ray diffraction study. The molecular structure of [Pd(k2-dppf)Cl2].CH2Cl2 complex is shown in Figure 1. The [Pd(k2-dppf)Cl2].CH2Cl2 complex crystallizes in a monoclinic space group Monoclinic, P21/c. a= 9.7960(3) A, b= 18.1527(7) A, c=19.0713(7) A, α= γ =90°, β=102.536(1). Structural analysis reveals that [Pd(k2-dppf)Cl2].CH2Cl2 complex has a square planer geometry around the metal center, two chlorines and two phosphorus atoms are coordinated with the palladium ion. The dppf behave as bidentate chelating ligand. The crystal determination data and selected bond distances and bond angles for [Pd(k2-dppf)Cl2].CH2Cl2 complex are summarized in Tables 4 and5. The palladium center was found to a distorted square planar geometry, with Cl1-Pd1-P1, Cl2-Pd1-P2, Cl1-Pd1-P2 and Cl2-Pd1-P1 angles of 87.79(2), 83.96(2), 171.50(3), and 177.75(2) respectively [30, 31].

The [Pd(k2-dppp)Cl2] complex was crystallized from a CH2Cl2 solution of the complex at room temperature, after a one week, as yellow colored needle type crystals are formed, these crystals were subjected to single-crystal X-ray diffractometer study. The molecular structure of [Pd(k2-dppp)Cl2] complex is shown in Fig. 2. The structural analysis reveals that [Pd(k2-dppp)Cl2] complex has a distorted square planer geometry around the metal center and that the two phosphorus and two chlorine atoms are coordinated to the palladium ion. The dppm behave as behave as bidentate chelating ligand. Whereas the Pd-P bond distance of 2.2424(4) and 2.2456(4) Ǻ for P(1) and P(2) atoms of the [Pd(k2-dppp)Cl2] complex30,31. The crystal determination data and selected bond distance and bond angles for [Pd(k2- dppp)Cl2] complex is summarized in Tables 4 and  6.

Figure 2: Molecular Structure of [Pd(k2-dppf)Cl2].CH2Cl2 Complex

Figure 2: Molecular Structure of [Pd(k2-dppf)Cl2].CH2Cl2 Complex



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The [Pt(k2-dppmCl)Cl2] complex was crystallized from a CH2Cl2 solution of the complex at room temperature, after a five days, a yellow colored needle type crystals are formed, these crystals were subjected to single-crystal X-ray diffractometer study. The molecular structure of [Pt(k2-dppmCl)Cl2] complex is shown in Fig. 3. The structural analysis reveals that [Pt(k2-dppmCl)Cl2] complex has a square planer geometry around the metal center and that the two phosphorus and two chlorine atoms are coordinated to the platinum ion. The dppm behave as behave as bidentate chelating ligand. Whereas the Pt-P bond length of 2.217(2) and 2.217(2) Ǻ for P(1) and P(2) atoms of the [Pt(k2-dppmCl)Cl2] complex30,31. The crystal determination data and selected bond distances and bond angles for [Pt(k2-dppmCl)Cl2] complex is summarized in Tables 4 and 7.

Figure 3: Molecular Structure of [Pd(k2-dppp)Cl2] Complex

Figure 3: Molecular Structure of [Pd(k2-dppp)Cl2] Complex



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Table 4: Crystallographic Data and structure refinement for [Pd(k2-dppf)Cl2].CH2Cl2, [Pd(k2-dppp)Cl2] and [Pt(k2-dppmCl)Cl2]complexes.

[Pd(k2-dppf)Cl2].CH2Cl2 [Pd(k2-dppp)Cl2]  [Pt(k2-dppmCl)Cl2]
Empirical formula C34H28Cl2FeP2Pd.CH2Cl2 C27H26Cl2P2Pd C24.27H21.46Cl2P2Pt(Cl)0.729 (H) 0.54
Formula weight 816.58 589.72 667.43
R 0.03 0.02 0.03
Temperature 200 K 200 K 200 k
Radiation 0.71073 A 0.71073 A 0.71073 A
Crstal system Monoclinic triclinic Monoclinic
space group P21/c P-1 C2/c
a(°A) 9.7960(3) 8.4865(3) 16.2034(5)
b(°A) 18.1527(7) 10.5484(4) 7.8274(2)
c(°A) 19.0713(7) 14.4020(6) 19.2496(6)
Α(deg) 90 88.388(2) 90
β(deg) 102.536(1) 80.064(2) 98.918(1)
γ(deg) 90 73.475(2) 90
volume 3310.5(2)A^3 1217.16(8) A^3 2411.92(12)A^3
F(000) 1640 596 4, 1.838 Mg/m^3
Z, Calculated density 4, 1.638 Mg/m^3 2, 1.609 g/m^3 6.263 mm^-1
Absorption coefficient 1.426 mm^-1 1.128 mm^-1 1288
Crystal size 0.41 x 0.46 x 0.47 mm 0.19 x 0.31 x 0.51 mm 0.04 x 0.20 x 0.21 mm
Dataset -13: 13 ; -20: 24 ; -25: 25 -11: 11 ; -13: 14 ; -18: 19 -13:21; -10:10; -25:25
Reflections collected / unique 60083,8203,[R(int)= 0.018] 32265, 6016,[R(int)= 0.016] 16294,3007,[R(int)= 0.030]
Observed Data [I > 2.0 sigma(I)] 7414 5668 2930
R, wR2, S R= 0.0284, wR2= 0.0693,S= 1.04 R= 0.0177, wR2= 0.0451, S= 1.03 R= 0.0478 wR2= 0.1178 S= 1.30
Min. and Max. Resd. Dens [-2.08, 1.73] e/Ang^3 [-0.44,0.44] e/Ang^3 [-1.71, 4.83] e/Ang^3
Max. and Av 0.00 and 0.00 0.00 and 0.00 0.00 and 0.00

 

Table 5: Selected bond distances (in A°) and bond angles (in degree) for [Pd(k2-dppf) Cl2].CH2Cl2

Bond distance

Bond angle

Pd(1)-Cl(1) 2.3417(7) Cl(1)-Pd(1)-P(1) 87.79(2)
Pd(1)-Cl(2) 2.3577(7) Cl(1)-Pd(1)-P(2) 171.50(3)
Pd(1)-P(1) 2.2774(7) Cl(2)-Pd(1)-P(1) 177.75(2)
Pd(1)-P(2) 2.2883(7) Cl(2)-Pd(1)-P(2) 83.96(2)
Fe(1)-C1(1) 1.996(2) P(1)-Pd(1)-P(2) 97.94(2)
Fe(1)-C1(2) 2.028(2) C1(3)-Fe-C1(4) 40.16(10)
P(1)-C1(1) 1.802(2) Pd(1)-P(1)-C(31) 108.46(7)

 

Table 6: Selected bond distances (in A°) and bond angles (in degree) for [Pd(k2-dppp)Cl2]

Bond distance Bond angle
Pd(1)-Cl(1) 2.3575(4) Cl(1)-Pd(1)-Cl(2) 90.54(1)
Pd(1)-Cl(2) 2.3557(4) Cl(1)-Pd(1)-P(1) 87.77(1)
Pd(1)-P(1) 2.2424(4) Cl(1)-Pd(1)-P(2) 177.80(2)
Pd(1)-P(2) 2.2456(4) Cl(2)-Pd(1)-P(1) 172.11(2)
P(1)-C(1) 1.8243(16) Cl(2)-Pd(1)-P(2) 91.39(1)
P(2)-C(3) 1.8355(16) P(1)-Pd(1)-P(2) 90.47(1)
C(3)-H(3)A 0.9900 Pd(1)-P(1)-C(1) 116.42(5)

 

Table 7: Selected bond distances (in A°) and bond angles (in degree) for [Pt(k2-dppmCl)Cl2]

Bond distance Bond angle
Pt(1)-Cl(1) 2.3661(19) Cl(1)-Pt(1)-P(2) 98.10(7)
Pt(1)-P(2) 2.217(2) Cl(1)-Pt(1)-P(1) 98.10(7)
Pt(1)-P(1) 2.217(2) Cl(1)-Pt(1)-Cl(1)_a 90.02(6)
Pt(1)-Cl(1)_a 2.3661(19) Cl(1)-Pt(1)-P(2)_a 171.58(7)
Pt(1)-P(2)_a 2.217(2) Cl(1)_a-Pt(1)-P(2) 171.58(7)
P(1)-C(21) 1.816(7) P(2)-Pt(1)-P(2)_a 73.87(8)
P(2)-C(11) 1.808(8) Pt(1)-P(1)-C(21) 117.2(3)

 

Scheme 1

Scheme 1

 


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Figure 4: Molecular Structure of [Pt(k2-dppmCl)Cl2] Complex

               Figure 4: Molecular Structure of [Pt(k2-dppmCl)Cl2] Complex

 



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Figure 5: The Proposed Geometrical Structure of [Pd(k2-dppp)(HSBIBT)Cl]Cl Complex Figure 5: The Proposed Geometrical Structure of [Pd(k2-dppp)(HSBIBT)Cl]Cl Complex

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Figure 6: The Proposed Geometrical Structure of [Pt(k2-dppmCl)(HSBIBT)Cl]Cl Complex Figure 6: The Proposed Geometrical Structure of [Pt(k2-dppmCl)(HSBIBT)Cl]Cl Complex

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Conclusions

In this research we have describe the synthesis and characterization of some Palladium and platinum complexes obtained from the reaction of the Thioester ligand with tertiary diphosphines metal complexes as shown in Figure 1. The manner of bonding and overall structure of complexes were determined through elemental analysis, magnetic susceptibility, molar conductance, IR spectral data and UV-Visible. All synthesized complexes are square planar and diamagnetic.

Acknowledgements

The authors are thankful to the chemistry Department. College of Education-Salahaddin University for their accomplishing our present work and Prof T.I.A. Gerber and Eric. C. Hosten at Nelson Mandela Metropolitan University for their help in obtaining the X-ray crystallographic data.

References

  1. Walia, R; Hedaitullah, M; Naaz, S.F.; Iqbal, K; Lamba, H. Int. J. Res. Pharm. Chem. 2011, 3, 565-574
  2. Vikash, K; Deveder, P. Int. Res. J. of Pharm. 2014, 12, 861-875
  3. Husain, A; Varshney, M; Rashid, M; Mishra, R; Akhter, A. J. of Pharm. Res. 2011, 2, 413-419
  4. Alias, M; Mahal, D. Int. J. of Sci. and Res. 2015, 7, 1469-1476
  5. Finšgar, M.Corr. Sci. 2013, 72, 90-98
  6. Anandara, K; Tiwari, R; Bothara, K; Sunilson, J; Dineshkumar, C; Promwichit, P. Adv. in App.Sci. Res. 2010, 2, 132-138
  7. Mor, M; Bordi, F; Silva, C; Rivara, S; Zuliani, V; Vacondio, F; Rivara, M; Barocelli, E; Bertoni, S; Ballabeni, V. Bioorg. Medi. Chem. 2004, 4,663-674
  8. Bakhareva, E; Voronkov, M; Sorokin, M; Lopyrev, V; Seredenin, S;  Gaidarov, G. Pharm. Chem. J. 1996, 2,89-91
  9. Anandara, K; Tiwari, R; Venkateshan, N; Pooshan, G; Promwichit, P. J. Chem and Pharm res. 2010, 3, 230-236
  10. Thakuria, H; Das, G. Arkivoc. 2008,15, 321-328
  11. Lobana, T; Sultana, R. J. Chem. Sci. 2012, 6, 1261-1268
  12. Kazemi, M; Shiri, L. J. Sulf. Chem. 2015, 6,1-11
  13. Pourshahbaz, M; Irandoust, M; Rafiee, E; Joshaghani, M. Polyhedron. 2009, 3, 609-613
  14. Cavell, R. Curr. Sci. 2000, 4, 441-452
  15. Lassahn, P; Lozan, V; Weller, A; Janiak, C. Dalton Trans. 2003, 23, 4437-4450
  16. APEX; SADABS; SAINT.2010, Bruker AXS Inc., Madison, Wisconsin, USA.
  17. Sheldrick, G.M. Acta Crystallogr. 2008, A 64, 112-122
  18. Hubschle, C. B.; Sheldrick, G.M.; Dittrich, B. J Appl Cryst. 2011, 44, 1281-1284
  19. Enaam, M. R. Diyala J. for Pure Sci. 2013, 1, 97-110
  20. Pessoa, J; Duarte, M; Gillard, R; Madeira, C; Matias, P; Tomaz, I. J. Chem Soc, Dalton Trans. 1998, 23, 4015-4020
  21. Amin, O; Al-Hayaly, L; Al-Jibori, S; Al-Allaf, T. Polyhedron. 2004, 11, 2013-2020
  22. Bu’itrus, N; Hussain, K. Asian J. of Chem. 2003, 4, 1617-1622
  23. Al-Jibori, S; Al-Jibori, M; Hogarth, G. Inorg. Chim. Acta. 2013, 398, 117-123
  24. Al-Hayaly, L; Abdullah, B. H.; Al-Dulaimi, A; Al-Jibori, S. A. Oriental J. of Chem. 2008, 2, 381-388
  25. Edwards. P; Jaouhari, R. Polyhedron. 1989, 1, 25-28
  26. Kumbhare, L; Jain, V; Varghese, B. Inorg. Chim. Acta. 2006, 2, 409-416
  27. Sutton, D. 1968 McGraw-Hill 192-
  28. Pastorek, R; Kameníček, J; Krystýnková, P; Šindelář, Z. Acta Universitatis Palackianae Olomucensis. 2000, 39, 63
  29. Al-Jibori, S; Abdullah, A; Al-Allaf, T. Tran. Metal Chem. 2007, 3,398
  30. Al-Jibori, S; Al-Jibori, Q; Schmidt, H; Merzweiler, K; Wagner, C; Hogarth, G. Inorg. Chim. Acta. 2013, 402, 69-74
  31. Steffen, W; Palenik, G. Inorg. Chem. 1976, 10, 2432-2439