Indian Streams Research Journal

Vol III Issue I Feb 2013 Impact Factor : 0.2105

ISSN No : 2230-7850 ORIGINAL ARTICLE

Monthly Multidisciplinary Research Journal

Indian Streams Research Journal

Executive Editor

Editor-in-chief

Ashok Yakkaldevi

H.N.Jagtap

IMPACT FACTOR : 0.2105 Welcome to ISRJ RNI MAHMUL/2011/38595 ISSN No.2230-7850 Indian Streams Research Journal is a multidisciplinary research journal, published monthly in English, Hindi & Marathi Language. All research papers submitted to the journal will be double - blind peer reviewed referred by members of the editorial Board readers will include investigator in universities, research institutes government and industry with research interest in the general subjects.

International Advisory Board Flávio de São Pedro Filho Federal University of Rondonia, Brazil

Hasan Baktir Mohammad Hailat English Language and Literature Dept. of Mathmatical Sciences, University of South Carolina Aiken, Aiken SC Department, Kayseri Kamani Perera 29801 Regional Centre For Strategic Studies, Sri Ghayoor Abbas Chotana Lanka Department of Chemistry, Lahore Abdullah Sabbagh University of Management Sciences [ PK Engineering Studies, Sydney Janaki Sinnasamy ] Librarian, University of Malaya [ Anna Maria Constantinovici Catalina Neculai Malaysia ] AL. I. Cuza University, Romania University of Coventry, UK Romona Mihaila Spiru Haret University, Romania

Ecaterina Patrascu Spiru Haret University, Bucharest

Delia Serbescu Spiru Haret University, Bucharest, Romania

Loredana Bosca Spiru Haret University, Romania

Anurag Misra DBS College, Kanpur Titus Pop

Fabricio Moraes de Almeida Federal University of Rondonia, Brazil George - Calin SERITAN Postdoctoral Researcher

Horia Patrascu Spiru Haret University, Bucharest, Romania Ilie Pintea, Spiru Haret University, Romania Xiaohua Yang PhD, USA Nawab Ali Khan College of Business Administration

Editorial Board Iresh Swami Pratap Vyamktrao Naikwade ASP College Devrukh,Ratnagiri,MS India Ex - VC. Solapur University, Solapur R. R. Patil Head Geology Department Solapur University, Solapur Rama Bhosale Prin. and Jt. Director Higher Education, Panvel Salve R. N. Department of Sociology, Shivaji University, Kolhapur Govind P. Shinde Bharati Vidyapeeth School of Distance Education Center, Navi Mumbai Chakane Sanjay Dnyaneshwar Arts, Science & Commerce College, Indapur, Pune

N.S. Dhaygude Ex. Prin. Dayanand College, Solapur Narendra Kadu Jt. Director Higher Education, Pune K. M. Bhandarkar Praful Patel College of Education, Gondia Sonal Singh Vikram University, Ujjain

Rajendra Shendge Director, B.C.U.D. Solapur University, Solapur R. R. Yalikar Director Managment Institute, Solapur Umesh Rajderkar Head Humanities & Social Science YCMOU, Nashik S. R. Pandya Head Education Dept. Mumbai University, Mumbai

Alka Darshan Shrivastava G. P. Patankar S. D. M. Degree College, Honavar, Karnataka Shaskiya Snatkottar Mahavidyalaya, Dhar Maj. S. Bakhtiar Choudhary Director,Hyderabad AP India.

Rahul Shriram Sudke Devi Ahilya Vishwavidyalaya, Indore

S.Parvathi Devi Ph.D.-University of Allahabad

S.KANNAN Ph.D , Annamalai University,TN

Awadhesh Kumar Shirotriya Secretary, Play India Play (Trust),Meerut Sonal Singh Address:-Ashok Yakkaldevi 258/34, Raviwar Peth, Solapur - 413 005 Maharashtra, India Cell : 9595 359 435, Ph No: 02172372010 Email: [email protected] Website: www.isrj.net

Satish Kumar Kalhotra

Indian Streams Research Journal Volume 3, Issue.1,Feb. 2013

Available online at www.isrj.net

ISSN:-2230-7850 ORIGINAL ARTICLE

“SYNTHESIS AND CHARACTERIZATION OF AZIDOBRIDGED CR, MO, W METAL CARBONYL COMPLEXES” AMIT SINGHAL , MANISH KAUSHIK, MUNESH KUMAR, MANOJ AGARWAL Department of Chemical Sciences, Jagdishprasad Jhabarmal Tibrewala University, Jhunjhunu, Rajasthan Department of Applied Sciences, Accurate Institute of Management & technology, Gr. Noida (U.P.) Department of Chemistry, Agrasen P.G. College, Sikandrabad, Bulandshahr (U.P.) Department of Applied Sciences, Accurate Institute of Management & technology, Gr. Noida (U.P.)

Abstract: We have synthesized nine polynuclear complexes {M(CO)3[L]}1a-1c, 2a-2c and 3a-3c (1a, M = Cr, L=L1, R = Me, R' = H; 1b, M = Mo, L=L1, R = Me, R' = H; 1c, M = W, L=L1, R = Me, R' = H; 2a, M = Cr, L=L2, R = Me, R' = Me; 2b, M = Mo, L=L2, R = Me, R' = Me; 2c, M = W, L=L2, R = Me, R' = Me; 3a, M = Cr, L=L3, R = Eth, R' = Eth; 3b, M = Mo, L=L3, R = Eth, R' = Eth; 3c, M = W, L=L3, R = Eth, R' = Eth) by photochemical d i s p l a c e m e n t o f t h re e C O g ro u p f ro m M ( C O ) 6 b y 4 - b ro m o - 2 - ( 2 methylaminoethylimino)methyl]phenol [L1], 4-bromo-2-(2-dimethyla minoethy limino)methyl]phenol [L2], 4-bromo-2-(2-diethylaminoethylimino)methyl]phenol [L3]. The synthesized complexes exhibit variable degree of antibacterial activity. The complexes have been characterized by elemental analysis, IR, [1H]-NMR spectroscopy and magnetic studies. The spectroscopic studies suggest a tridentate behavior of the ligand with the metal (0). KEYWORDSSchiff bases, coordination chemistry, azido-bridge complexes, antibacterial activity. INTRODUCTION Metal-organic complexes containing bridged ligands are of current interest because of their continued interest due to their interesting molecular structure and their different functionalities [1-7]. Due to the versatile coordination modes of the ambidentate thiocyanate and azide ligands, these pseudohalide ligands have become the most extensively studied building blocks in the multi-dimensional complexes [89]. We have synthesized polynuclear complexes of the type 1a-1c, 2a-2c and 3a-3c (1a, M = Cr, L=L1, R = Me, R' = H; 1b, M = Mo, L=L1, R = Me, R' = H; 1c, M = W, L=L1, R = Me, R' = H; 2a, M = Cr, L=L2, R = Me, R' = Me; 2b, M = Mo, L=L2, R = Me, R' = Me; 2c, M = W, L=L2, R = Me, R' = Me; 3a, M = Cr, L=L3, R = Eth, R' = Eth; 3b, M = Mo, L=L3, R = Eth, R' = Eth; 3c, M = W, L=L3, R = Eth, R' = Eth) has been synthesized by photochemical displacement of three CO groups in group-6 metal carbonyls with 4-bromo-2-(2methylaminoethylimino)methyl]phenol [L1], 4-bromo-2-(2-dimethylaminoethylimino)methyl]phenol [L2], 4-bromo-2-(2-diethylaminoethylimino)methyl]phenol [L3]. Both the ligands & their complexes were characterized on the basis of physical properties, elemental analysis data, magnetic studies, infrared and nuclear magnetic resonance spectroscopy. It was found that the ligands have tridentate nature coordinating through two N and one O atom. Thus replacing 1,5-cyclooctadiene to maintain charge density on metal Title : “SYNTHESIS AND CHARACTERIZATION OF AZIDO-BRIDGED CR, MO, W METAL CARBONYL COMPLEXES” Source:Indian Streams Research Journal [2230-7850] AMIT SINGHAL , MANISH KAUSHIK, MUNESH KUMAR, MANOJ AGARWAL yr:2013 vol:3 iss:1

“SYNTHESIS AND CHARACTERIZATION OF AZIDO-BRIDGED ..............

centre. R' Br

N N

R

OH

2-((E)-(2-(dialkylamino)ethylimino)methyl)-4-bromophenol EXPERIMENTAL Reactions were carried out under dry argon or in vacuo. All solvents were dried and degassed prior to use. Infrared spectra were recorded on a Perkin-Elmer spectrophotometer (Model-577) in KBr discs and CH2Cl2. All the melting points were determined in an open capillary and are uncorrected. All glassware was oven dried at 120oC, molecular weight of the complexes were determined cryoscopically in benzene, cyclooctadiene (COD), n-hexane, n-pentane, benzene were purchased from E. Merck, and M(CO)6 (M = Cr, Mo, W), dichloromethane were purchased from Aldrich and were used as supplied. Magnetic susceptibility measurements of the complexes were carried out by Gouy method. UV irradiation were performed with a medium pressure 400W mercury lamp through a quartz bulb. SYNTHESIS OF THE LIGANDSSynthesis of ligand 4-bromo-2-(2-methylaminoethylimino)methyl]phenol [L1] The ligand 4-bromo-2-(2-methylaminoethylimino)methyl]phenol [L1] was prepared by literature method [7] as followed. 201.0 mg, (1.0 mmol) of 4-bromosalicyaldehyde and 74.1 mg (1.0 mmol) N,Nmethylethane-1,2-diamine was dissolved in 50ml Methyl alcohol at room temperature. On condensation brown colored ligand was found which was recrystallized using methyl alcohol. Yield 88.7%. Analysis Calc. for C10H13BrN2O Mol. Wt. 257.3, C, 46.71; H, 5.10; N, 10.89; Br, 31.08 found Mol. Wt. 256.2, C, 45.97; H, 4.90; N, 10.19; Br, 30.88. The other ligands were prepared similarly. H N

Br N

OH

2-((E)-(2-(methylamino)ethylimino)methyl)-4-bromophenol Preparation of complexes Preparation of complex {Cr(CO)3[L1]} The Cr(CO)6 (0.110 g, 0.5 mmol) and L1 (0.128 g, 0.5 mmol) were dissolved in DMF (40-50 cm3). The solution was irradiated for 3 h. During the irradiation, the color of the reaction mixture changed from colourless to dark yellow. After the irradiation, the reaction mixture was evaporated under vacuum, yielding a dark yellow solid. After dissolving in CH2Cl2 (10 cm3), petroleum ether (50 cm3) was added, resulting in the precipitation of a dark yellow solid which was washed with petroleum ether and dried under

Indian Streams Research Journal • Volume 3 Issue 1 • Feb 2013

2


vacuum. Yield of [Cr(CO)3 (L1)] : 67%. The other tricarbonyl complexes of Cr, Mo, W with L1, L2, L3 were prepared similarly. H N

Br N

Cr

O

O H O O

Scheme 1 – Preparation of Ligand: Reaction of 4-bromosalicyaldehyde with N,N-methylethane-1,2diamine at room temperature Br

H N

O +

H N

Br N

H 2N

OH

4-bromosalicyaldehyde

OH

N,N-methylethane -1,2-diamine

4-bromo-[2-(2-methylaminoethylimino) methyl]phenol

Scheme 2 – Preparation of Complexes: Reaction of 4-bromo-[2-(2-methylamino ethylimino) methyl] phenol with M(CO)6 [M= Cr, Mo, W] O

H N

Br

O

N

H N

Br N

Cr

+ OH

O

O

Cr

O

O H

O

O 4-bromo[-2-(2-methylaminoethylimino) chromium hexa carbonyl 1 methyl]phenol [L ]

O O

[Cr(CO)3 (L 1)]

Table 1a – Physical and analytical data of Ligands (L1-3) Molecular

Found (Calcd.) (%) Yield (%) M.p. (o C)

Ligands Formula a (L1)

b (L2 )

c (L3)

C10 H13 BrN2 O

C11 H15 BrN2 O

C13 H19 BrN2 O

69

74

72

146

154

159


Mol.

Colour C

H

N

Wt.

46.1

4.9

10.7

256.7

(46.7)

(5.1)

(10.9)

(257.1)

48.1

5.0

9.9

270.1

(48.7)

(5.6)

(10.3)

(271.2)

51.7

6.1

9.0

298.1

(52.2)

(6.4)

(9.4)

(299.2)

light yellow

Yellow

Cream

3


Table 1b – Physical and analytical data of Complexes {M(CO)3[L1-3]}(L = 4-bromo-2-(2methylaminoethylimino)methyl]phenol [L1], 4-bromo-2-(2-dimethylaminoethylimino)methyl]phenol [L2], 4-bromo-2-(2-diethylaminoethylimino)methyl]phenol [L3]) (M = Cr, Mo, W) Found (Calcd.) (%)

M olecular Co mplexes

Y ield (% )

M .p. (o C)

Formula 1a

C 13 H 10 BrCrN 2O 4

2a

C 13 H 10 BrM oN 2 O4

3a

C 13 H 10 BrW N 2O 4

1b


2b

C 14 H 12 BrM oN 2 O4

3b

C 14 H 12 BrW N 2O 4

1c


2c

C 16 H 16 BrM oN 2 O4

3c

C 16 H 16 BrW N 2O 4

68

64

69

66

68

66

65

60

68

M ol.

Colour

146

C

H

N

W t.

39.1

3.2

6.8

391.9

(39.7)

(3.3)

(7.1)

(393.1)

24.1

2.9

15.9

392.8

(35.7)

(3.0)

(6.4)

(437.9)

29.5

2.3

4.9

523.9

(29.7)

(2.5)

(5.3)

(525.0)

35.1

4.6

15.3

404.3

(35.4)

(4.9)

(15.8)

(406.7)

36.7

3.2

5.7

450.1

(37.3)

(3.4)

(6.2)

(451.9)

31.0

2.4

4.8

538.1

(31.2)

(2.8)

(5.2)

(539.0)

43.7

4.2

6.2

433.5

(44.1)

(4.4)

(6.4)

(435.2)

39.7

3.8

5.6

479.0

(40.1)

(4.0)

(5.8)

(479.9)

33.2

3.3

4.5

566.1

(33.9)

(3.4)

(5.0)

(567.0)

Light Ye llow

154

Ye llow

165

Ye llow

147

Light Ye llow

155

Ye llow

166

Cream

147

Light Ye llow

156

Ye llow

166

Cream

Tab le 2a. S elected IR bands (cm – 1 ) and (1 H)-NM R (p pm) data o f L 1 -3 ligand s S elected IR bands (cm -1 ) Ligand

Imine

amine

í (C= N)

í (NH )

1

H -N M R (in CD Cl3) ä p pm

3.4 1 (t, 2H , -CH 2 -), 2. 62 (t, 2H , -CH 2 -), 1

16 05

32 20

2.77( s, 3 H, -CH 3), 1. 60 (s, 1 H , -N H ), 10. 82 (s, 1 H , -O H) 3. 55 (t, 2 H, -CH 2 -), 2 .5 4 (t, 2 H , -CH 2-), 2.2 5

2

16 02

32 18 (s, 3 H , 5 -CH 3), 10 .7 4 (s, 1H, -OH ) 3. 57 (t, 2 H, -CH 2 -), 2 .5 9 (t, 2 H , -CH 2-), 1.0 9

3

16 04

32 21

(t, 3H, -CH 2 CH 3 ), 2 .79 (q , 2H , -CH 2 CH 3), 10.7 5 (s, 1H, -O H)


3


Table 2b. Selected IR bands (cm–1) and (1H)-NMR (ppm) data of complexes {M(CO)3[L1-3]}(L = 4-bromo2-(2-methylaminoethylimino)methyl]phenol [L 1 ], 4-bromo-2-(2-dimethyla minoethylimino) methyl]phenol [L2], 4-bromo-2-(2-diethylaminoethylimino)methyl]phenol [L3]) (M = Cr, Mo, W)

Sele cted IR bands ( cm-1)

Complex í (CO)

1a

Imine

amine

í (C=N)

í (NH)

1574

3201

2010, 1904, 1874

1

H-NM R (in CDCl3) ä ppm

3.71 (t, 2H, -CH 2-), 2.91 (t, 2H, -CH2-), 2.45( s, 3H, -CH3)

1b

2013, 1903, 1870

3.67 (t, 2H, -CH 2-), 2.92 (t, 2H, -CH2-), 2.47( s, 1575

3198 3H, -CH3)

1c

2015, 1901, 1869

3.65 (t, 2H, -CH 2-), 2.91 (t, 2H, -CH2-), 2.46( s, 1577

3202 3H, -CH3)

2a

2011, 1903, 1868

3.65 (t, 2H, -CH 2-), 2.72 (t, 2H, -CH2-), 2.27( s, 1570

3195 3H, -CH3)

2b

2017, 1893, 1858

3.67 (t, 2H, -CH 2-), 2.74 (t, 2H, -CH2-), 2.26( s, 1572

3192 3H, -CH3)

2c

2012, 1900, 1861

3.66 (t, 2H, -CH2 -), 2.73 (t, 2H, -CH2-), 2.25 (s, 1574

3197 3H, -CH3)

3a

2015, 1901, 1869

3.65 (t, 2H, -CH 2-), 2.72 (t, 2H, -CH 2-), 1.01 (t, 1577

3202 3H, -CH 2CH3), 2.40 (q, 2H, -CH 2CH3)

3b

2011, 1903, 1868

3.64 (t, 2H, -CH 2-), 2.73 (t, 2H, -CH 2-), 1.01 (t, 1570

3195 3H, -CH 2CH3), 2.41 (q, 2H, -CH 2CH3)

3c

2017, 1893, 1858

3.67 (t, 2H, -CH 2-), 2.74 (t, 2H, -CH 2-), 1.01 (t, 1572

3192 3H, -CH 2CH3), 2.42 (q, 2H, -CH 2CH3)

RESULTS AND DISCUSSION The ligands were prepared by condensation reaction of 4-bromo-salicylaldehyde with corresponding N,N-dialkylethane-1,2-diamine according to Scheme-1. Complexes (1a-3c) were prepared by photochemical reaction as shown in Scheme-2. Analytical data for {M(CO)3[L1]} (1a-1c); {M(CO)3[L2]} (2a-2c) and {M(CO)3[L3]} (3a-3c); where (M= Cr, Mo & W); complexes are given in Table1b. In this study, photochemical reactions of M(CO)6 (M=Cr, Mo & W) with 4-bromo-2-(2-methyla minoethylimino) methyl]phenol [L1], 4-bromo-2-(2-dimethylaminoethylimino)methyl]phenol [L2], 4bromo-2-(2-diethylaminoethylimino)methyl]phenol [L3] ligands occurs in expected manner, and gave hither to a series of complexes (1a)-(1c); (2a)-(2c) and (3a)-(3c) occur via the displacement of three CO from M(CO)6 (M=Cr, Mo & W) and co-ordination of metal atom via imine-N, amine-N and phenol-O donor atoms yielding M(CO)3L complexes. The i.r. spectra of ligands and the corresponding complexes provide information about the metalligand bonding. Important IR spectral bands M(CO)3L (L = 4-bromo-2-(2-methyla minoethylimino) methyl]phenol [L1], 4-bromo-2-(2-dimethylaminoethylimino)methyl]phenol [L2], 4-bromo-2-(2-diethyla minoethylimino) methyl]phenol [L3] and M=Cr, Mo & W) are presented in Table-2b. The evidence about metal-imine nitrogen (M–N) bond formation is the shifting of C=N vibration found at 1620cm-1 in free Indian Streams Research Journal • Volume 3 Issue 1 • Feb 2013

3


ligand, shifts to lower wavelength in complexes 1a-3c, showing that the ligand coordinate to metal via the imine donor atom [10]. The stretching vibrations found at 3020cm-1 in free ligand, shifts to lower wavelength in complexes showing that the ligand is coordinating via amine donor atom. In the proton NMR spectra of 1a-3c, the phenolic OH signal disappeared which is in agreement with the formation of metal oxygen bond [11-12]. In addition, the shift of the C-O stretching vibrations in the IR spectrum shows that both imine and amono N and phenolic O donor atoms coordinate to M atom. According to the these data, L1, L2 & L3 ligands behave as tridentate in 1a-3c. The L1, L2 & L3 ligands must act as a 6-electron donor in order to satisfy the 18-electron rule. Three bands in the range (2010-2024 cm–1), (1855-1948 cm–1) and (1787-1856 cm–1) arising from í (CO) vibrations are seen which presumably have local C2í symmetry of M(CO)3 unit in {M(CO)3L1} (1a1c); {M(CO)3L2}(1b-3b) and {M(CO)3L3} (1c-3c); where (M= Cr, Mo & W); complexes (Scheme-2). These values are in close resemblance to the values of í (CO) vibration for other sulfur containing disubstituted group-6 metal carbonyls [13-16]. The presence of normal ligand bands indicated that these bands were intact in the complexes. The nature and number of CO bands resemble closely to the bands of other known trisubstituted metal carbonyls [17, 18]. In addition, magnetic susceptibility measurement shows that (1a-3e) complexes were diamagnetic. Since these complexes have M(0) [M=Cr, Mo, W] with a low spin d6 configuration. Such diamagnetism might arise from further splitting of the d-orbital in the low symmetry complexes i.e. dxy2, dxz2, dyz2, d(x2-y2)0, dz2 0 [19, 20]. ANTIBACTERIAL ACTIVITY All the synthesized complexes were screened for their antibacterial activity by using agar diffusion method [21] against S. aureus , B. subtile gram positive and E. coli, S. paratyphi gram negative bacteria in nutrient agar medium. Ciprofloxacin was used as standard drug for comparison. These schiff's Bases and their metal carbonyl complexes show antibacterial activity against E. coli, S. aureus, B. subtile and S. paratyphi. It is found that 4-bromo-2-(2-methy laminoethy limino)methyl]phenol [L1] studied here follow such a decomposition scheme in the cell, and diazoalkane intermediates further could alkylate the nucleophilic centres of biologically important macromolecules and in particular DNA. 4-bromo-2-(2-dimethylaminoethylimino)methyl]phenol [L2], 4-bromo-2-(2diethylaminoethylimino)methyl]phenol [L3] shows moderate activity. With the help of activity data it could be observed that complexes M(CO)3L1(1a-1c) showed good activity against E.coli and S. paratyphi. Complexes M(CO)3L2 (2a-2c) and M(CO)3L3 (3a-3c) exhibited good activity against S. paratyphi. CONCLUSION The IR spectroscopic data are in well accord with a cis-chelating tridentate coordination of the ligand [22]. L1, L2 & L3 ligands behave as a tridentate ligand via imine and amine N and phenolic O donor atom in 1a-3c. In view of above, we have now investigated the nine new complexes 1a-3c, which have been prepared for the first time, by the photochemical reaction of metal carbonyls M(CO)6 (M=Cr, Mo & W), with 4-bromo-2-(2-alkylaminoethylimino)methyl]phenol (L1,L2,L3). The results show that 4-bromo-2-(2-alkylaminoethylimino)methyl]phenol and its metalcarbonyl derivatives exert a moderate inhibitory effect on different bacterial activity, thus confirming our previous data about the cytotoxic activity of these compounds. ACKNOWLEDGEMENTS Sincere thanks are due to Head, Dept. of Chemistry, A. I. M. T., Greater NOIDA, Head, Dept. of Chemical Sciences, JJTU, Rajasthan and Gaurav Pharma Limited, Pitampura, New Delhi for providing research facilities. Authors are also thankful to Dr. Vivek Kumar, Professor, IIT Roorkee, (Saharanpur Campus) for his constant encouragement to carry out such research work. Special thanks are also due to CDRI, Lucknow, Intertek, Mumbai, I.I.T., Roorkee, Research Lab, Delhi University and TIFR, Mumbai for allocation of time for various analyses. REFERENCES: 1.H. Abourahma, B. Moulton, V. Kravtsov, M.J. Zaworotko, J. Am. Chem. Soc., 124, 9990 (2002), A. Singh, M. Kumar, M. Kaushik, Int. J. Applied Chem., 6(1), 49-58 (2010) Indian Streams Research Journal • Volume 3 Issue 1 • Feb 2013

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2.S. R. Batten, R. Robson, Angew. Chem., 110, 1558 (1998). 3.S. R. Batten, R. Robson, Angew. Chem. Int. Ed., 41, 1561 (2002). 4.S. Konar, P.S. Mukherjee, E. Zangrando, F. Lloret, N.R. Chaudhuri, Angew. Chem., 114, 1631 (2002). 5.S. Konar, P.S. Mukherjee, E. Zangrando, F. Lloret, N.R. Chaudhuri, Angew. Chem. Int. Ed., 41, 1561 (2002). 6.S.K. Dey, N. Mondal, M.S. El. Fallah, R. Vicente, A, Escuer, X. Solans, M. Font-Bardia, T. Matsushita, V. Gramlich, S. Mitra, Inorg. Chem., 43, 2427 (2004). 7.You Z-L & Zhu H-L, Z. Anorg. Allg. Chem., 632, 140 (2006). 8.S. K. Dey, N. Mondal, M.S. El Fallah, R. Vicente, A. Escuer, X. Solans, M. Font-Bardia, T. Matsushita, V. Gramlich, S. Mitra, Inorg. Chem., 43, 2427 (2004). 9.S. Sailaja, K. R. Reddy, M. V. Rajasekharan, C. Hureau, E. Riviere, J. Cano, J-J. Girerd, Inorg. Chem., 42, 180 (2003). 10.J. E. Kovacic, Spectrochim, Acta 23A, 182 (1967). 11.H.K. Duggal, B.V. Agarwala, Spectrosc Lett. 21, 1 (1988). 12.N . Karacan, Z. Kantarer, S. Akyuz, Spectrochim. Acta Part A, 52, 771 13.S. W. Kirtley, in G. Eilkinson, F. G. A. Stone, E. W. Abel, (eds): “Comprehensive Organometallic Chemistry”, Pergamon Press, Oxford, Vol. 3, p 1079, 1255 (1982). 14.A. S. Cavallo, G. Solladie, E. Tsano, Journal of Organometallic Chemistry, 144, 181 (1978). 15.R. Lal Sc. K. Samanta (nee Bera), I. Banerjee, Indian Journal of Chemistry, 40A, 144 (2001). 16.W. Kaim, S. Kohlmann, Inorganic Chemistry, 26, 68 (1987). 17.Cotton F.A., Kraihanzel, C.S., J.Am. Chem. Soc., 84, 4432 (1962). 28. Zahida OZER, Saim. OZKAR, Turk. J. Chem., 23, 9-14, (1999). 18.Timmers, F.J., Wacholtz, W.F., J.Chem. Ed., 71, 987 (1994), King, R.B., Organometallic Syntheses, Vol. 1, Academic Press, New York, 125(1965); Abel E., Bennett, W.M.A., Burton, R. Wilkinson G., J. Chem. Soc., 4559 (1958). 19.Senem Karahan, Ploinkose, and Elif Subasi Hamdi Temel; Synthesis and reactivity in Inorganic, Metalorganic, and Nano-Metal Chemistry, 38, 422-427 (2008). 20.Ayodhya Singh, Munesh Kumar, Manish Kaushik, Seema Singh and Anjali Singh; Oriental Journal of Chemistry, 26(2), 601-606 (2010). 21.A. L. Barry, “The antimicrobial susceptibility Test: Principal and practice”, Edited by Illus Lea and Febiges, Philadelphia, Pa. U.S.A., 148-193 (1976). 22.Meek, D.W. and Niepon, P., J. Am. Chem. Soc., 87, 4951 (1965).


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