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Organocobalt Complexes of Diacetylmonoxime Buckled

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Organocobalt Complexes of Diacetylmonoxime Buckled Indian Journal of Chemistry Vol. 39A, December 2000, pp. 1312-1316 Organocobalt complexes of corresponding organo derivatives (IV-VII and IX­ diacetylmonoxime buckled with different XIII) are given in Fig. I. diamines as 'models' for vitamin B 12 Experimental derivatives All the solvents used were of AR grade, cobalt(II) chloride hexahydrate (Qualigens), I ,2-diamino K Hussai n Reddy', M Radhakrishna Reddy & K Mohana Raju t benzene and 3,4-diaminotoluene (FLUKA AG), Department of Chemistry, Sri Krishnadevaraya University, diacetylmonoxime (Spectrochem AR), iodomethane Anantapur 515 003, India (Merck), bromoethane (Merck), pyridine (Qualigens) Received 16 March 1999; revised 15 October 1999 and imidazole (Spectrochem, AR) were used in the present study. Macrocyclic chlorocobalt complexes have been synthesized using preformed li gands viz. bis(diacetyl monoxime)-1 ,2- phenylenediimine (I) and bis(diacetyl monoxime)-3 ,4-tolylene­ Synthesis of ligands I and I.l diimine (II). The chloro derivatives have been alkylated using In a I 00 cm3 short-necked round-bottomed flask, iodomethane and bromomethane in the presence of pyridine or I diacetyl-monoxime (3.76 g, 0.037 mol) was taken in and imidazole. The alkyl derivatives have been characterized by 3 elemental analysis, conductivity data, magnetic susceptibility methanol ( 15 cm ) and to this was added diamine measurements, electronic and infrared spectral data and they are (2 g, 0.0185 mol) in methanol and heated under reflux found to be I: I electrolytes. Various ligand fi eld parameters like for I h. The reaction mixture was cooled and Dq •Y, Dq'· and Dt have been calculated. Infrared spe<.:tra reveal the coloured compound obtained was recrystallized from 'trans effect' in these complexes. Electrochemical behaviour of these complexes has been studied by cyclic voltammetry. There has been growing interest in organocobalt complexes which might serve as 'model compounds' for coenzyme B 12. Cobalt complexes of diacetylmonoxime buckled with diamines 1 appear to mimic the properties of coenzyme B 12 better than the complexes of tetradentate Schiff base li gands, perhaps, as in the former the equatorial ligand can act I ![ as ligand of the uninegative charge and posesses pseudo symmetry as corrin. Synthesis of organocobaloxime with modified structural features continues to be a fascinating area in the chemistry of model compounds of coenzyme B 12 . Recently, Gupta and Rol reviewed the synthetic aspects of organocobaloxime chemistry. In view of the above relevance and in continuation of our investigations on axial ligational properties of cobalt complexes3.4, herein we report the synthesis, characterization, spectral and electrochemical studies Jtl R = B = Cl Vlll R = B = Cl B C H N IX R ~ CH ; B = C H N on macrocyclic 'organocobalt complexes' of IV R = CH3 ; = 5 5 3 5 5 R = CH ; B:: c H N X CH ; B: c H N bis(diacetylmonoxime)-1 ,2-phenylenediimine (I) and v 3 3 4 2 R" 3 3 4 2 VI R = c H ; B: C H N XI R = C H ·;s= C H N bis-(diacetylmonoxime)-3,4-tolylenediimine (II). The 2 5 5 5 2 5 5 5 VII · R = c H ; B= c H N XII R. ~ c H ; B =c H N structures of chloro derivatives (Ill, VIII) and 2 5 3 4 2 2 5 3 4 2 Fig. !-Structures of ligands (I & II), chloro complexes (III & t Dcpartme~t of Polymer Science and Technology, S K University, VIII) and organocobalt complexes (IV-VII, IX-XII). III & VIII Anantapur, India are neutral complexes. C5H5N =Pyridine, C3H4N2 =Imidazole NOTES 1313 warm ethanol. The colours, melting points together The elemental analyses were performed by the with elemental analyses are given in Table I . HERAEUS (Mikro standard 8304071) elemental analyzer. The magnetic susceptibility measurements Synthesis of th e chloro complexes III and VIII were made using a vibrating sample magnetometer The reaction mixture containing ligand (0.004 (VSM) operating at a field strength of 2 KG to 8 KG . mol)and cobalt(II) chloride hexahydrate (0.004 mol) The molar conductance of complexes in (DMF) 3 3 in methanol (30 cm ) was refluxed with stirring for (Ca. -10- M) were determined at 27± 2°C using a 1 h. The resulted green solution was filtered and kept Systronic 303 direct reading conductivity bridge. The overnight at room temperature. The dark green 1H-NMR spectra were recorded on an AMX-400 compound which separated out was filtered and MHz high resolution NMR instrument in acetone-d6 washed repeatedly with acetone followed by diethyl solvent at room temperature. The electronic spectra ether to get the dark green compound. for all complexes in UV region ( 180-1100 nm) were recorded with Schimadzu UV -160A spectrophoto­ Synthesis of organocobalt complexes IV-VII and IX­ meter in methanol. The IR spectra were recorded in XII the ranges 4000-400 (in KBr) and 450-50 cm-1 (in In a Schlenk tube, a saturated methanolic solution polyethylene) using Brucker IFS 66V FT-IR of macrocyclic cobalt complex (III) or (VIII) (0.004 spectrophotometer. The cyclic voltammetry was mol) was taken and stirred under nitrogen performed with a BAS model CV -27 controller and a atmosphere. Alkylation reaction was carried out by conventional three electrode configuration with using CH31/C2H5Br as described in the standard glassy carbon working electrode, silver/silver 7 procedure . The colour, melting points, and molar chloride reference electrode and platinum counter conductance for all complexes are given in Table I. electrode. Nitrogen was used as a purge gas and all Table 1-Colour, elemental analyses and magnetic moment data of the cobalt complexes (B.M.) Colour Found (Calcd) % rcJT11 c H N I C,4HI RN40 2 Yellow 61. 05 6.71 19.95 (178-180) (6 1.30) (6.6 1) (20.43) II C,sH2oN40 2 Light pink 62.35 6.91 19.51 (169-171) (62.50) (6.94) ( 19.44) III [Co(C t4H t7N40 2)CI 2l Grey green 41.95 4.23 13.94 Diamagnetic (242D) (41.71) (4.25) ( 13.90) IV [CH 3Co(C14H 17 N40 2)C5H5N]CI Dark green 51.92 5.55 15 .03 0.22 (>300) (51.89) (5.62) (15.13) v [CH3Co(C,4H11N402)C3H4N2]Cl Snuff 47.71 5.48 18.75 0.72 (246 D) (47.75) (5.54) ( 18.61 ) VI [C2H3Co(C 14H 17 N40 2)C5H5N]CI Light brown 52.98 5.76 14.72 Di amagnetic (295 D) (52.89) (5.88) (14.69) VII [C2H5Co(C,4Ht1N402)C3H4H2]Cl Brown 48.87 5.9 1 18.10 0.12 (206 D) (48.99) (5.80) (18.04) VIII [Co(C15H ,~N402)Cl2 Brownish green 43 .12 4.62 13.35 0.48 (2 14-216) (43 .07) (4.79) (13 .40) IX [CH3Co(C15 H ,~N 4 0 2 )C 5 H 5 N]Cl Dark brown 52.76 5.81 14.76 0.52 (290 D) (52.89) (5.88) (14.69) X [CH 3Co(C15 H ,9N402)C3H4N2]Cl Black 49.06 5.91 17.96 0.77 (277 D) (48.99) (5.80) (18.04) XI [C2HsCo(C 1sH ,9N402)C5HsN]Cl Dark brown 53.71 6.15 14.76 Diamagnetic (> 300) (53.83) (6.12) (14.60) XII [C 2 H 5 Co ( C, 5 H,~N 4 02 )( C 3 H4N 2 ]CI Light brown 49.99 6.15 17.45 Diamagnetic (265 D) (50.66) (6.04) ( 17.52) 1314 INDIAN J CHEM., SEC. A, DECEMBER 2000 solutions were 0.1 M concentration in TBAP. residual amount of paramagnetic susceptibility (Table 1). This may be arised by the distortion of Results and discussion groups by their neighbours due to the existence of The infrared spectra of ligands I and II show no electron energy levels very close to that of ground characteristic absorption bands assignable to either state. C=O (or) NH2 groups indicating the formation of The electronic spectra of the dichloro complexes ligands. Strong bands appearing in the region 1584- are recorded in DMF. These complexes exhibit three 1 6 1576 cm- are attributed to v(C=N) in both ligands • d-d transitions, two in the visible and one in the near The strong as well as sharp bands at 1220 em-I are UV -region, characteristic of tetragonally distorted 7 due to the N-0 stretching vibration. The strong bands octahedral cobalt(III) complexes . The crystal field observed around -775 cm-1 are assigned to C=N-0 model of Wentworth and Piper16 has been employed deformation vibration. Bands characteristic of methyl to interpret the electronic absorption bands. In the groups of diacetylmonoxime are observed in the present study, the D 411 crystal field model has been 1454-1458 [Vasy(C-CH,)] and 1380-1386 cm-1 [Vasy chosen as its spectral characteristics are analogous to (C-CH3)]regions in the IR spectra of both ligands. those of complexes with D 411 microsymmetry. The phenyl ring exhibits several bands in the lower The two bands exhibiting in the visible region, energy region. Thus the bands at 1260, 1130 and 990 15552, 17090 cm- 1 and 21367, 22075 cm-1 are 1 cm- are attributed to the phenyl group. The broad attributable to the transitions 1A 1 .~: -~ 1E/ (vE) and 1 bands at around 2900 cm- are assigned to v(OH) 1 1 A 1K --t A 2 ~: (vA) in the dichloro complexes III and vibrations of the li gands. VIII respectively. The calculated DlY, Dt and Dqz Both ligands are characterized by high resolution based on these assignments are 2517, 2583; 570, 663 1 1 6 (400 MHz) H-NMR spectra in acetone-d6.
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