Magnetic and Structural Studies of Complexes of IsonitrosopropiophenoneThiocarbonohydrzoneBenzaldehydeswith Ni (II), Pd (II) and Pt(II)

 

Dilip C. Sawant*, R.G.Deshmukh

Department of Chemistry, Konkan GyanpeethKarjat College of Arts, Science and CommerceKarjat,

Raigad, Maharashtra, INDIA

*Corresponding Author E-mail: dcsawant@rediffmail.com,ravideshmukh@vsnl.net

 

ABSTRACT:

A novel Ni(II), Pd(II) and Pt(II) complexes of Isonitrosopropiophenonethiocarbonohydrzone benzaldehydes derived from N”-[(1Z,2E)-(hydroxyimino)-1-phenylpropylidene]thiocarbonohydrazide (HTIPP)and substituted benzaldehydes, have been synthesized and studied. Six new ligands are reported herein using two electron withdrawing (-Cl, -NO2) and two electron donating (-OH,-OCH3) substituents benzaldehyde and HTIPP.  Their structures have been discussed on the basis of spectral, magnetic and powdered X-ray crystallography studies.The dimeric nature of the complexes supported by molecular weight determinations by Rast method. The result so obtained suggest binuclear distorted octahedral geometry for Ni(II) complexes, while mononuclear square planar geometry for Pd(II) and Pt(II) complexes. The room temperature magnetic susceptibility measurements reveals that antiferromagnetic interactions exists between the high spin Ni(II) ions within the dinuclear unit. The powdered X-ray crystallography study reveals orthorhombic crystal system for Ni(II) complexes.

 

KEYWORDS:Binuclear Ni(II) complexes,Pd(II), Pt(II), antiferromagnetism, distorted octahedral, square planar

 

 


INTRODUCTION:

In a continuation of our works[1-3] we undertook investigation of Ni(II), Pd(II) and Pt(II) complexes of Isonitrosopropiophenonethiocarbonohydrzone benzaldehydes derived from benzaldehyde with N”-[(1Z,2E)-(hydroxyimino)-1-phenylpropylidene]thiocarbonohydrazide (HTIPP).These complexes are interesting because of the ligands having strong donor atoms such as azomethine nitrogen, oximino oxygen and thione sulfur.

 

 

 

 

 

 

The schiff base HTIPP exists in two tautomeric forms, thione and thiol tautomer’s. All the complexes of HTIPP reported[3] reveal that the sulfur atom does not take part in coordination, probably due to the predominance of the thione tautomer over the thiol one.

 

It is premised that the thione-thiol tautomerism could be shifted to the thiol dominance so as to involve sulfur atom in coordination with the metal ion.Padhye et[4] al reported that these types of ligand interacting with transition metal ions depends upon the presence of an additional coordination center in the ligand moiety and the charge on the ligand is influence by the thione-thiol equilibrium.It is proposed that reacting the free amino group in HTIPP with a compound containing an aldehyde group may affect the thione-thiol tautomerism making available the sulfur atom for coordination with the metal ion. This is expected to yield complexes with changed structural features and interesting biological or analytical applications[5-10].The nature of these groups like steric properties, electronic properties, and the geometric properties affect the metal orbitals and thus affect its properties[11].

 

In the present paper, the preparation and properties of complexes of Ni(II), Pd(II) and Pt(II) with benzaldehyde derivatives of schiff base HTIPP are reported. The structure of these complexes have been discussed on the basis the results of conductance, magnetic, spectral and powdered X-ray studies.

 

EXPERIMENTAL:

Physical Measurements:

The elemental analyses were carried by standard methods[12]. Infrared spectra were recorded on a Jasco FTIR 4600 spectrophotometer in the spectral range of 4000-400cm-1. Electronic spectra were measured on Equiptronic EQ-824 spectrophotometer in dimethyl formamide solution at KGKC Karjat. The molar conductance measurements of the complexes in dimethyl formamide (DMF) were obtained using an Equiptronic EQ-660 conductivity meter. Magnetic susceptibility measurements were carried out by employing Gouy’s balance using Hg(Co(SCN)4] as calibrant at Institute of Science Mumbai. The effective magnetic moments were calculated after diamagnetic correction for ligand component using Pascal’s constants. The powdered XRD pattern of all Co(II) complexes recorded in the 2q range of 10 to 80° at a wavelength 1.5406A° using Cuka radiation source by MiniFlex II desktop X-ray Diffractometer at TIFR Mumbai.

 

Synthesis of the ligands and metal complexes:

The substituted benzaldehydes derivatives of HTIPP was prepared by following the procedure described earlier[1-2] using 4-methoxybenzaldehyde; 2-hydroxybenzaldehyde; 2-chlorobenzaldehyde; 4-chlorobenzaldehyde; 3-nitrobenzaldehyde; 4-nitrobenzaldehyde abbreviated as HIPTB2toHIPTB7 respectively.

 

Following general method was adopted for the synthesis of all Ni(II) complexes:

An ethanol solution of two moles ligand was reacted with ethanol solution of one mole NiCl2.6H2O. The reaction mixture was refluxed for 3 hours, cooled, filtered, washed with ethanol and neutralized with excess hot water, dried and recrystallized to give a desired Ni(II) complex.

 

Typical procedure for preparation of [Ni(IPTB2)2]2Cl2:

An ethanol solution (10cm3) containing 1.005g (0.0042M) of NiCl2.6H2O was treated with ethanol solution (50cm3) of 3.201g (0.0087M) ligand HIPTB2. The reddish-brown precipitate obtained, was shake well for 10-15minutes at room temperature and digest at refluxed temperature for 3hours. Further cooled to room temperature, filtered, washed with ethanol and neutralized with excess hot water, dried at 110ºC and re-crystallised from chloroform.

 

Following general method was adopted for the synthesis of all Pd(II) and Pt(II)complexes:

The Pd(II) complex was formed by the addition of an ethanol solution of ligandto a solution of palladium chloride in dilute HCl and digesting the mixture on a hot water bath for about 30 minutes. It was filtered, washed with water, dried at 110ºC.

 

The Pt(II) complex was formed by the addition of an ethanol solution ligandto a solution of chloroplatinic acid in dilute HCl and digesting the mixture on a hot water bath for about 30 minutes. It was filtered, washed with water, dried at 110ºC.


 

RESULTS:

Table I: Analytical data and Physical properties

Compounds

Molecular Formula

FWT

Yield

%

Colour

D.

Pt.

ºC

Elemental analysis [Found(Expected)]

Molar

Conductance

(in DMF)

Magnetic

moment

(meff)

%M

%C

%H

%N

%S

%Cl

Scm2/mol

BM

[Ni(IPTB2)2]2Cl2

C72H72Cl2Ni2N20O8S4

1662

62.41

Red

212

6.51

(7.06)

51.55

(51.98)

4.27

(4.33)

17.18

(16.84)

7.24

(7.70)

4.68

(4.27)

67.16

1.17

[Ni(IPTB3)(HIPTB3)Cl]2

C68H67Cl2Ni2N20O8S4

1608

83.58

Red

215

6.95

(7.30)

50.56

(50.75)

4.02

(4.16)

17.81

(17.41)

8.12

(7.96)

4.61

(4.42)

34.70

2.56

[Ni(IPTB4)(HIPTB4)Cl]2

C68H62Cl6Ni2N20O4S4

1682

39.80

orange

240

6.19

(6.98)

48.35

(48.51)

3.41

(3.68)

17.05

(16.65)

7.42

(7.61)

12.16

(12.66)

57.58

1.00

[Ni(IPTB5)(HIPTB5)Cl]2

C68H62Cl6Ni2N20O4S4

1682

68.19

Red

240

6.52

(6.98)

48.28

(48.51)

3.39

(3.68)

17.02

(16.65)

7.82

(7.61)

12.16

(12.66)

58.74

1.18

[Ni(IPTB6)(HIPTB6)Cl]2

C68H62Cl2Ni2N24O12S4

1724

53.69

Red

210

6.09

(6.80)

47.21

(47.33)

3.52

(3.60)

19.71

(19.49)

7.72

(7.42)

5.07

(4.12)

24.24

1.22

[Ni(IPTB7)(HIPTB7)Cl]2

C68H62Cl2Ni2N24O12S4

1724

58.83

Red

228

6.59

(6.80)

47.22

(47.33)

3.47

(3.60)

19.67

(19.49)

7.73

(7.42)

4.87

(4.12)

22.44

0.93

Pd(IPTB2)2

C36H35N10O4PdS2

842.27

67.37

brown

255

12.55

(12.63)

-

-

-

-

absent

9.23

Dia

magnetic

Pd(IPTB3)2

C34H31N10O4PdS2

814.22

72.29

brown

235

12.80

(13.07)

-

-

-

-

absent

19.94

Dia

magnetic

Pd(IPTB4)2

C34H29N10Cl2O2PdS2

851.11

72.74

brown

233

12.20

(12.50)

-

-

-

-

absent

11.00

Dia

magnetic

Pd(IPTB5)2

C34H29N10Cl2O2PdS2

851.11

61.32

brown

253

12.21

(12.50)

-

-

-

-

absent

11.38

Dia

Magnetic

 

Pd(IPTB6)2

C34H29N12O6PdS2

872.22

63.36

brown

262

11.86

(12.20)

-

-

-

-

absent

11.47

Dia

magnetic

Pt(IPTB2)2

C36H35N10O4PtS2

930.94

66.67

light

yellow

256

20.52

(20.95)

-

-

-

-

absent

7.16

Dia

magnetic

Pt(IPTB3)2

C34H31N10O4PtS2

902.88

66.13

light

yellow

237

20.96

(21.60)

-

-

-

-

absent

10.09

Dia

magnetic

 

Table II: selected ir bands for ligands and its Ni(II), Pd(II) and Pt(II) complexes

Compounds

n(O-H) oxime

n(N-H)

n(C=N)

(azomethine)

n(C=N)

(oxime)

n(HC=N)

imino

n(C-N)

C=NOH

>N-C=S

C=S + C=C

n(C=S) + n(C=C)

n(N-O) C=NOH

d(C-S)

>N-C=S

 

[Ni(IPTB2)2]2Cl2

-

3048

1598

1576

-

1484

1257

1168

1014

826

[Ni(IPTB3)(HIPTB3)Cl]2

3317

3173

1603

1573

1538

1486

1284

-

1009

782

[Ni(IPTB4)(HIPTB4)Cl]2

3261

3181

1608

1562

1519

1488

1287

1125

1009

757

[Ni(IPTB5)(HIPTB5)Cl]2

3261

3180

1607

1561

1521

1482

1289

1158

1012

767

[Ni(IPTB6)(HIPTB6)Cl]2

3266

-

1610

1566

1522

1491

1285

1273

1009

767

[Ni(IPTB7)(HIPTB7)Cl]2

3259

3184

1591

1566

1513

1488

1285

-

1008

767

Pd(IPTB2)2

3257

3195

1603

1563

1529

1487

1286

1178

1008

784, 811

Pd(IPTB3)2

3317, 3273

3174

1617

1570

1531

1473

1287

1179

1006

749,

Pd(IPTB4)2

3265

3115

1590

1538

-

1491

1280

1133

1006

749,

Pd(IPTB5)2

-

3194

1594

1564

1519

1487

1286

1135

1008

767

Pd(IPTB6)2

3257

3183

1617

1565

1519

1488

1285

1135

1008

767

Pt(IPTB2)2

3258

3195

1603

1562

1529

1488

1286

1178

1008

784, 811

Pt(IPTB3)2

3317,3273

3174

1617

1570

1531

1473

1287

1178

1006

749,

 

Table IIIA: electronic spectra of Ni(II) complexes (in cm-1)

Complexes

Charge transfer

S ®Ni(II)

Charge Transfer

azomethine

N àNi(II)

3A2gà3T2g

(v1) Calc.

3A2gà

3T1g(F) (v2)

3A2gà

3T1g(P) (v3)

3A2gà1Eg

Dq

B

b

Dq/B

v2/v1

j-value

[Ni(IPTB 2)2]2Cl2

25641

(e=5376)

21277

(e=7950)

7229

11494

(e=17.04)

18519

(e=8645)

-

722.9

555.0

0.539

1.302

1.590

-279.7

[Ni(IPTB 3)(HIPTB 3)Cl]2

25000

(e=4783)

21789

(e=6209)

6963

11494

(e=17.46)

20000

(e=6631)

15625 (e=869)

696.3

707.1

0.686

0.985

1.651

-

[Ni(IPTB 4)(HIPTB 4)Cl]2

-

21739

(e=6682)

7186

11765

(e=27.08)

20000

(e=7154)

14286

(e=316)

718.6

 

680.5

0.661

1.056

1.637

-338.8

[Ni(IPTB5)(HIPTB5)Cl]2

-

22222

(e=7082)

7325

11765

(e=38.33)

19231

(e=7680)

14925

(e=524)

732.5

601.4

0.584

1.218

1.606

-288.7

[Ni(IPTB 6)(HIPTB 6)Cl]2

-

22222

(5890)

6243

10526

(e=12.05)

20000

(e=6424)

-

624.3

786.4

0.764

0.794

1.686

-256.2

[Ni(IPTB 7)(HIPTB 7)Cl]2

-

23810

(e=7396)

6432

10753

(e=37.68)

19608

(e=8128)

-

643.2

737.7

0.716

0.872

1.672

-433.3

 

Table IIIB: electronic spectra of complexes (in cm-1)

Complexes

1A1gà1B1g

Spin-spin forbidden

Spin-spin forbidden

Magnetic momentmeff, BM

Pd(IPTB 2)2

20202cm-1 (e=365.2)

18519cm-1 (e=313.2)

14184cm-1 (e=27.8)

Diamagnetic

Pd(IPTB 3)2

20000cm-1 (e=366.9)

17544cm-1(e=134.3)

14388cm-1 (e=26.4)

Diamagnetic

Pd(IPTB 4)2

19048cm-1 (e=406.5)

-

13333cm-1 (e=11.0)

Diamagnetic

Pd(IPTB 5)2

21739cm-1 (e=353.6)

18182cm-1 (e=154.8)

14286cm-1 (e=26.9)

Diamagnetic

Pd(IPTB 6)2

20833cm-1 (e=353.9)

18349cm-1 (e=268.2)

14085cm-1 (e=26.5)

Diamagnetic

Pt(IPTB 2)2

22026cm-1 (e=372.0)

17730cm-1 (e=126.9)

-

Diamagnetic

Pt(IPTB 3)2

21786cm-1 (e=374.5)

18051cm-1 (e=122.4)

-

Diamagnetic

 

Table IV: Crystallographic data for Ni(II) complexes

Molecular formula

[Ni(IPTB 2)2]2Cl2

[Ni(IPTB 3)(HIPTB 3)Cl]2

[Ni(IPTB 4)(HIPTB 4)Cl]2

Crystal system

Orthorhombic

Orthorhombic

Orthorhombic

Space group

Pbmn

Pbmn

Pbmn

l (A°)

1.5406

1.5406

1.5406

Reflections

29

35

29

2q (deg) maxima

19.778

19.8754

11.0262

‘d’ (A°) maxima

4.4852

5.2283

8.4348

Unit cell dimensions

 

 

 

a (A°)

9.8092

9.0550

14.6095

b (A°)

9.6326

9.1362

14.5830

c (A°)

10.1424

8.8623

14.6231

A (A°)

0.00616

0.00723

0.00278

B (A°)

0.00639

0.00710

0.00279

C (A°)

0.00576

0.00755

0.002775

α (°)

90

90

90

b (°)

90

90

90

g (°)

90

90

90

Unit cell Volume, V (A°3)

958.348

733.169

3115.47

Density, d (g/cm3)

5.799

7.33

3.396

Particle size (nm)

1.7538

1.7695

1.6442

q ranges °

15-72

16-79

10-61

Intensity (Arb. unit)

5-258

7-98

8-172

 

Molecular formula

[Ni(IPTB5)(HIPTB5)Cl]2

[Ni(IPTB 6)(HIPTB 6)Cl]2

[Ni(IPTB 7)(HIPTB 7)Cl]2

Crystal system

Orthorhombic

Orthorhombic

Orthorhombic

Space group

Pbmn

Pbmn

Pbmn

l (A°)

1.5406

1.5406

1.5406

Reflections

42

21

37

2q (deg) maxima

21.5336

18.9729

19.8435

‘d’ (A°) maxima

5.7973

6.9186

7.5256

Unit cell dimensions

 

 

 

a (A°)

10.0426

11.9814

13.0328

b (A°)

9.3281

12.0320

12.8637

c (A°)

10.6083

11.6373

13.0380

A (A°)

0.00588

0.00413

0.00349

B (A°)

0.00682

0.0041

0.00359

C (A°)

0.00527

0.00438

0.00349

α (°)

90

90

90

b (°)

90

90

90

g (°)

90

90

90

Unit cell Volume, V (A°3)

993.775

1677.659

2185.84

Density, d (g/cm3)

5.4147

3.4313

2.6336

Particle size (nm)

1.7200

1.6236

1.7213

q ranges °

15-77

12-56

11-74

Intensity (Arb. unit)

6-157

13-211

7-169

 


DISCUSSIONS:

The elemental analysis data (Table I) indicates ML2 formation of these complexes. The isolated solid complexes are stable in air and their high decomposition temperatures (>200°C) indicates strong metal-ligand bond.The molar conductance data reports that all complexes are non-conducting except Ni(II) complex of HIPTB2. The molecular weight determination by Rast method suggesting dimeric nature of the Ni(II) complexes.

 

Spectral Studies:

IR spectra (4500-500cm-1) of ligands and metal complexes are given in a Table II. As discussed earlier ligands can exhibit thione-thiol tautomerism since it’s containthioamide>NH-C=S functional group. The absence of n(S-H) bandin ligands indicates thione form of ligand in solid state. The band appearing in range749-826cm-1in the spectrum of the electron donating substituted ligandsdue to d(C-S) are shifted to lower wavenumber in complexation indicating that thione sulfur behaves as donor group[13].Whereas electron withdrawing substituted HIPTB4-HIPTB7ligands complexation with Ni(II) and Pd(II), the nC=S stretching vibrations are not altered and seen as its usual position indicating non participation of thione sulfur.[14]. In other hand complexation the azomethine bands shift to lowering frequencies of up to 27cm-1indicating coordination through azomethine nitrogen[15]. In addition coordination via nitrogen of the azomethine groupis indicated by a shift towards higher side of bands corresponding to d(C-N-N) at about 1300-1400cm-1.A common feature of all complexesis absence of oximino –OH stretching vibrations or weak band with shifting to lower frequencies revealing that the anion of the ligands occurs or forms by the deprotonation of the one or both oximino group[16]. The metal-nitrogen and metal-oxygen bands appeared at 573-522 cm-1, 513-506cm-1 respectively which are not observed in spectrum of the free ligand.[17]

 

Magnetic properties:

The room temperature magnetic moments of binuclear Ni(II) complexes in the range 0.93-2.56 B.M., which are lower than the respective spin only values indicating antiferromagnetic coupling interaction.[18-20]These arises due to the magnetic exchange interaction in such a complex occurs when the neighboring magnetic centers are close enough for direct or indirect orbital overlap. The exchange coupling constant ‘J ’ values of Ni(II) complexes of HIPTB2, HIPTB4-HIPTB7 are -279.70; -338.81; -288.78; -256.26; -433.35 respectively suggested coupling type is strongly antiferromagnetic.

 

Observed diamagnetism of Pd(II) and Pt(II) is suggestive square planar geometry, supported by electronic spectral spectra.

 

The electronic spectra:                                                  

The electronic spectra of the complexesin dimethyl formamide solution are characterized by absorption bands at 6243-7325 cm-1 (calculated), 10526-11765 cm-1and 19231-20000cm-1for Ni(II) complexeswhich may be ascribed to the allowed transitions 3A2g(F)à3T2g(F) (n1),3A2g(F)à3T1g(F) (n2), and 3A2g(F)à3T1g(P) (n3) respectively, characteristic of octahedral geometry.Another weak band observed at 14000-16000cm-1corresponding to 3A2gà1Eg transition suggested distorted octahedral geometry for these complexes.[21]The ratio of 1.59-1.68 for n2/n1is consistent with the assignment [18,22-24]. Various ligand field parameters like Dq, B and b, calculated on the basis of equations given by E.Konig,suggestedconsiderable amount of covalent character of the Metal-Ligand bond in proposed structure. In addition of these bands, two bands in the range 25641-25000cm-1 and 21277-23810cm-1observed in Ni(II) complexes attributed to a charge transfer transition. These bands indicating sulfur-to-nickel SàNi charge transfer[25-26] and nitrogen-to-nickel NàNi charge transfer bands [14]respectively. It is noteworthy that sulfur-to-metal charge transfer band is not observed in the metal complexes of electron withdrawing substituted benzaldehyde derivatives, HIPTB4-HIPTB7.

 

The electronic spectra of diamagnetic Pd(II) and Pt(II) complexes exhibit bands at 19048-22026cm-1 assigned to 1A1gà1B1g transition, typical square planar geometry[27]. Another weak bands observed in range 18182-18519cm-1and 13333-14388cm-1in Pd(II) and 17730cm-1 in Pt(II) complexes due to spin-spin forbidden transition.

 

Powder X-ray diffraction studies:

All the main peaks have been indexed by using appropriate methodology[28-29] and use of computer program (Winplotr). The 2q values and relative intensities corresponding to the prominent peaks, unit cell parameters, crystal size, and density have been listed in Table IV. The unit cell lattice parametersa, b, c, a, b, gand volume v belongs to orthorhombic system and space group is Pbmn. The complexes have the average crystal size of 1.6 to 1.8 nm suggesting nanocrystalline nature.

 

On the basis of the present investigation the dimeric form sulfur coordinated and not coordinated Ni(II) complexes may be represented by the structure (Fig.1).

 

 

 

 

Fig 1: Sulfur coordinate and non-coordinate Ni(II) complexes

 

On the basis of the present investigation the Pd(II) and Pt(II) complexes may be represented by the structure (Fig.2).

 

 

Fig 2: sulfur coordinated Pd(II), Pt(II) and sulfur non-coordinate Pd(II) complexes

                                 

CONCLUSION:

The analytical and physico-chemical analyses confirm the composition and the structure of the newly obtained complexes. The physical, spectral, and magnetic studies indicates Ni(II) complexes are in a binuclear system where every atom of Ni(II) are hexa-coordinated through oximino-bridge. Whereas Pd(II) and Pt(II) are square planar geometry. The properties of the antiferromagnetic interactions of binuclear Ni(II) complexes can be described as a super exchange between nickel centers through double spin exchange interaction between the magnetically active atomic orbitals of the nickel ion and the non-bonding p-MO of the oximino bridges. All Ni(II) complexes are found to possess an orthorhombic crystal system.

 

ACKNOWLEDGEMENTS:

The Authors wish to thank Department of Chemistry, Konkan GyanpeethKarjat College of Arts, Science & Commerce teaching and non-teaching staff, Niraj Bahuguni for encouraging and support. Also thank to Dr.P.D.Babu from UGC-DAE, BARC Mumbai for VSM data, Dr.N.Kulkarni from TIFR Mumbai and Dr.Malge from Institute of Science Mumbai for powdered XRD data, Dr.R.M.Patil from Institute of Science for magnetic susceptibility and his guidance. Also thankful to SAIF, IIT Mumbai for the PMR, ESR, TGA-DTA data.

 

CONFLICT OF INTEREST:

The authors declare that we have no conflict of interest.

 

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Received on 30.03.2018         Modified on 12.04.2018

Accepted on 21.04.2018         © AJRC All right reserved

Asian J. Research Chem. 2018; 11(4):717-722.

DOI:10.5958/0974-4150.2018.00127.X