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Physicochemical, spectral, and biological studies of Mn(II), Cu(II), Cd(II), Zr[(OH).sub.2] (IV), and U[O.sub.2](VI) compounds with ligand containing thiazolidin-4-one moiety.

1. Introduction

There are numerous biologically active molecules with five membered rings, containing two heteroatoms among which is the 4-thiazolidinone ring system which is a core structure in various synthetic compounds.

Thiazolidin-4-one, a saturated form of thiazole with carbonyl group on fourth carbon, has been considered as a magic moiety (wonder nucleus). It has played an important role in medicinal chemistry [1, 2] and posseses almost all types of biological activities [3, 4] like antimicrobial [5], antitubercular [6], antibacterial [7], anticonvulsant [8], antifungal [9], anticancer [10], septicidal [11], and antiviral [12]. Much attention has been paid to biologically active metal complexes in recent years. Oxygen and nitrogen donor ligands [13] have been widely studied due to their high potential to coordinate with transition metals. Compounds containing carbonyl oxygen groups [14] have important position among organic reagents as potential donor ligands for the transition metal ions. Organic compounds and metal complexes [15] both display a wide range of pharmacological activities including anticancer, antibacterial, and fungi static effects.

A perusal of the literature indicates that very less work have been carried out on the coordination compounds of the thiazolidinones [16,17] and there is no report on the coordination compounds of Mn(II), Cu(II), Cd(II), Zr[(OH).sub.2](IV), and U[O.sub.2](VI) ions with N-(2-carbamoylthienyl)-C-(3'-carboxy-2,-hydroxyphenyl)thiazolidin-4-one, L[H.sub.3] (II).

In this paper, we describe the syntheses, characterization, and antibacterial studies of II and its coordination compounds.

The structures of Schiff base (I) and thiazolidin-4-one (II) are shown in Figures 1 and 2 respectively.

2. Experimental

2.1. Materials. Copper(II) acetate monohydrate (S d FineCHEM Limited); cadmium(II) acetate dihydrate, dioxouranium(VI) acetate tetrahydrate, and manganese(II) acetate tetrahydrate (Sarabhai); mercaptoacetic acid, dry benzene, sodium bicarbonate (Ranbaxy); thiophene-2-carboxylic acid hydrazide (Acros Organics, USA) were used as received for the syntheses. 3-Formylsalicylic acid and hexadecaaquaoctahydroxotetrazirconium(IV) acetate were synthesized by following the reported procedures [18].

2.2. Analyses and Physical Measurements. The organic skeleton of the respective coordination compounds were decomposed by the slow heating of ~0.1g of the latter, with conc. HN[O.sub.3]. The residue was dissolved in minimum amount of conc. HCl and the corresponding metal ions were estimated as follows. The Mn(II) and Cd(II) contents of the respective coordination compounds were estimated by complexometric titration method against standardized EDTA solution using eriochrome black-T and xylenol orange as the indicators, respectively. The Cu(II) content was estimated iodometrically against a standard solution of sodium thiosulphate to the starch end point. The zirconium content was estimated gravimetrically as Zr[O.sub.2] after decomposing the corresponding compound with a few drops of conc. HN[O.sub.3] and then igniting the residue. The uranium content in [U[O.sub.2](LH)] was estimated gravimetrically as [U.sub.3][O.sub.8] after decomposing the compound with a few drops of conc. HN[O.sub.3] and then igniting the residue.

The C, H, and N contents of L[H.sub.3] and its coordination compounds were determined by CHN Eager analyzer model300. The S and Cl contents of L[H.sub.3] and its coordination compounds were estimated gravimetrically as BaS[O.sub.4] and AgCl, respectively. The molecular weight measurements were carried out by the Rast method using diphenyl as the solvent [19]. The molar conductances ([[LAMBDA].sub.M]) of the coordination compounds were measured in DMF with the help of a Toshniwal conductivity bridge (CL01-02A) and a dip-type cell calibrated with KCl solutions. The IR spectra were recorded in KBr pellets (4000-400 [cm.sup.-1]) on a Beckman-20 spectrophotometer. The reflectance spectra were recorded on a Beckmann DU spectrophotometer attached with a reflectance arrangement. The magnetic susceptibility measurements were carried out at room temperature, using Hg[Co[(NCS).sub.4]] as the standard [20]. The diamagnetic corrections were computed using Pascal's constants. The magnetic susceptibilities were corrected for temperature-independent paramagnetism term (TIP) [20] using value of zero for Mn(II) ions and 60 x [10.sup.-6] cgs units for Cu(II) ions.

2.3. Synthesis of Schiff Base, N-(2-Carbamoylthienyl)-3'-carboxy-2'-hydroxybenzylideneimine (I). A MeOH solution (30 mL) of thiophene-2-carboxylic acid hydrazide (1.42 g, 10 mmol) was added to a MeOH solution (30 mL) of 3-formylsalicylic acid (1.66 g, 10 mmol). The mixture was refluxed for 2h and the precipitates formed were suction-filtered, washed with and recrystallized from MeOH, and dried in vacuo at room temperature over silica gel for 24 h. Yield = 80%. The elemental analyses of the title compound gave the satisfactory results.

2.4. Synthesis of N-(2-Carbamoylthienyl)-C-(3'-carboxy-2'-hydroxyphenyl)thiazolidin-4-one (II). A dry benzene solution of I (2.90g, 10mmol) and mercap to acetic acid (0.92g, 10 mmol) were refluxed for 12 h on a water bath. The mixture was cooled to room temperature and then washed with 10% sodium bicarbonate solution. The benzene layer was separated using a separating funnel. The evaporation of the excess of solvent gave the solid product which was recrystallized from petroleum ether. The compound was dried in vacuo at room temperature. Yield = 16%. Anal: (II, [C.sub.15][H.sub.12][N.sub.2][O.sub.5][S.sub.2]) (obsd: C, 49.15%; H, 3.10%; N, 7.50%; S, 17.30%. Calcd.: C, 49.45%; H, 3.30%; N, 7.69%; S, 17.58%); IR bands (KBr): 2855 [cm.sup.-1] [v(O-H) (intramolecular H-bonding)], 1690 [cm.sup.-1] [v(C=O) (thiazolidinone ring)], 1675 [cm.sup.-1] [v(C=O) (carboxylic)], 1648 [cm.sup.-1] [v(C=O) (amide)], 1570 [cm.sup.-1] [v(C-N) (thiazolidinone ring)], 1530 [cm.sup.-1] [v(C-O) (phenolic)], 820 [cm.sup.-1] [v(C-S) (thiazolidinonering)], and 640 [cm.sup.-1] [v(C-S) (thiophene ring)].

2.5. Syntheses of the Coordination Compounds of II. A MeOH solution (30-50 mL) of the appropriate metal salt (10 mmol) was added to a MeOH solution (50 mL) of II (3.64 g, 10 mmol) and the mixture was then refluxed for 3-4 h. The solid products formed were suction-filtered, washed with MeOH, and then dried as mentioned above. Yield = 35-55%.

3. Results and Discussion

A dry benzene solution of the Schiff base I reacts with mercaptoacetic acid and forms N-(2-carbamoylthienyl)-C-(3'-carboxy-2'-hydroxyphenyl)thiazolidin-4-one, L[H.sub.3] (II). The reaction of the latter with appropriate metal salts in 1 : 1 molar ratio in MeOH produces the coordination compounds: [Mn(LH)[(MeOH).sub.2]], [[Cu(LH)].sub.2], [Cd(LH)], [Zr[(OH).sub.2][(OAc).sub.2] (L[H.sub.3])], and [U[O.sub.2](N[O.sub.3])(L[H.sub.2])(MeOH)]. The compounds are stable in air at room temperature. They are partially soluble in MeOH and EtOH and completely soluble in dMsO and DMF. Their molar conductance measurements ([[LAMBDA].sub.M] = 4.6-10.3 mho [cm.sup.2] [mol.sup.-1]) indicate their nonelectrolytic nature. The analytical data of II and its coordination compounds are given in Table 1.

3.1. Infrared Spectral Studies. The infrared spectra of I, II and the coordination compounds of the latter were recorded in KBr and the prominent peaks (in [cm.sup.-1]) are shown in Table 2. I exhibits the v(C=N) (azomethine) stretch at 1635 [cm.sup.-1]. This band disappears in II and a new band appears at 1570 [cm.sup.-1] due to the v(C-N) (thiazolidinone ring) stretch [21] indicating the conversion of I into II. The formation of II is further supported by the appearance of a new band at 820 [cm.sup.-1] due to the v(C-S) (thiazolidinone ring) stretch [22]. The v(C-N) (thiazolidinone ring) stretch of II shifts to lower energy by 55 and 65 [cm.sup.-1] in [Mn(LH)(MeOH)2] and [Cd(LH)], respectively, suggesting the involvement of the thiazolidinone ring N atom towards coordination [22]. However, the existence of this band at the same energy in the remaining coordination compounds indicates the noninvolvement of the thiazolidinone ring N atom towards coordination. II exhibits a strong band at 2855 [cm.sup.-1] due to the intramolecular H-bonded OH groups of phenolic and/or carboxylic acid moieties [23]. The appearance of this band almost at the same energy in the coordination compounds of the Zr[(OH).sub.2](IV) and U[O.sub.2](VI) ions is indicative of the noninvolvement of the OH groups of the above moieties towards coordination. On the other hand, the coordination compounds of the rest of the metal ions do not show this band indicating the breakdown of H-bonding and subsequent deprotonation of the OH groups followed by the involvement of phenolic and carboxylic O atoms towards coordination. The v(C=O) (thiazolidinone ring) stretch [24] of II occurs at 1690 [cm.sup.-1]. This band shifts to 1645 and 1660 [cm.sup.-1] in the coordination compounds of Zr[(OH).sub.2](IV) and U[O.sub.2](VI) ions indicating the coordination through O atom of the carbonyl group of thiazolidinone moiety. However, the above band remains unchanged in the rest of the coordination compounds suggesting the noninvolvement of the above O atom towards coordination. The v(C=O) (carboxylic) stretch [25] of II occurs at 1675 [cm.sup.-1]. This band remains unchanged in the coordination compounds of Zr [(OH).sub.2](IV) and U[O.sub.2](VI) ions indicating the noninvolvement of the O atom of carboxylic group towards coordination. However, the remaining coordination compounds display two new bands between 1550-1575 [cm.sup.-1] and 1340-1365 [cm.sup.-1]. These bands are assigned to the [v.sub.as](COO) and [v.sub.s](COO) stretches of the carboxylato ligand. The energy separation ([DELTA]v = 210-218 [cm.sup.-1]) between the [v.sub.as](COO) and [v.sub.s](COO) stretches is indicative of the monodentate nature of the carboxylato ligand [26]. The presence of a strong band at 1648 [cm.sup.-1] due to the v(C=O) (amide) stretch in II indicates that it occurs in the keto form [27]. This band shifts to lower energy by 20 and 35 [cm.sup.-1] in [Mn(LH)[(MeOH).sub.2]] and [Cd(LH)], respectively, suggesting the involvement of the keto O atom towards coordination. However, the existence of this band at the same energy in the remaining coordination compounds indicates the noninvolvement of the keto O atom towards coordination. The v(C-O)[PHI] stretch [28] (1530 [cm.sup.-1]) of II undergoes a positive shift by [less than or equal to] 10 [cm.sup.-1] in the coordination compounds of Mn(II) and Cd(II) ions, while it shifts to 20 [cm.sup.-1] in [[Cu(LH)].sub.2]. This band remains unchanged in the remaining compounds indicating the noninvolvement of phenolic O towards coordination. The v(C-S) (thiazolidinone ring) stretch [21] of II shifts from 820 [cm.sup.-1] to lower energy by 35 [cm.sup.-1] in [[Cu(LH)].sub.2], suggesting the formation of bond between the metal ions and the S atom. However, it remains unchanged in the rest of the coordination compounds indicating the noninvolvement of S atom towards coordination.

The v(C-S) (thiophene moiety) stretch [21] of II occurs at 640 [cm.sup.-1]. The appearance of a band at the same energy in the coordination compounds of Mn(II), Cu(II), and Cd(II) ions favours the noninvolvement of S atom of thiophene moiety towards coordination. On the other hand, the negative shift by 60 and 45 [cm.sup.-1] of this band in [Zr[(OH).sub.2] [(OAc).sub.2](L[H.sub.3])] and [U[O.sub.2](N[O.sub.3])(L[H.sub.2])(MeOH)], respectively, indicates the coordination through S atom of thiophene moiety. The presence of a broadband between 3300 and 3400 [cm.sup.-1] due to v(O-H)(MeOH) stretch and the decrease of v (C-O)(MeOH) stretch [28] from 1034 [cm.sup.-1] to lower energy by 35 and 49 [cm.sup.-1] in [Mn(LH)[(MeOH).sub.2]] and [U[O.sub.2](N[O.sub.3]) (L[H.sub.2])(MeOH)], respectively, indicate the involvement of the O atom of MeOH towards coordination 28].

The absence of a band in the region 835-955 [cm.sup.-1] due to the v(Zr=O) stretch [29] in the present Zr[(OH).sub.2](IV) compound suggests its formulation as [Zr[(OH).sub.2][(OAc).sub.2](L[H.sub.3])] and not as [ZrO([H.sub.2]O)[(OAc).sub.2](L[H.sub.3])] [25]. The presence of a broadband at 3445 [cm.sup.-1] due to coordinated OH group and the appearance of a new medium intense band at 1125 [cm.sup.-1] due to the [delta](Zr-OH) bending mode [25] also support the proposed structure of the present Zr(IV) compound. The acetato ligand is coordinated to the metal ion in a monodentate fashion [30] as evident by the appearance of two new bands at 1580 and 1365 [cm.sup.-1] due to the [v.sub.as](acetate) and [v.sub.s](acetate) stretches, respectively, in the spectrum of [Zr[(OH).sub.2][(OAc).sub.2](L[H.sub.3])]. [U[O.sub.2](N[O.sub.3])(L[H.sub.2])(MeOH)] exhibits the [v.sub.as](O=U=O) stretch [31] at 920 [cm.sup.-1]. The force constant ([f.sub.U-O]) and U-O bond length in the present compound are 7.03 mdyn/[Angstrom] and 1.73 [Angstrom], respectively [25].

Nitrate group is associated with [D.sub.3h] symmetry in free ion and exhibits three IR active vibrations: [v.sub.2] (820 [cm.sup.-1]), [v.sub.3] (1380 [cm.sup.-1]), and [v.sub.4] (700 [cm.sup.-1]). The [D.sub.3h] symmetry of the free nitrate ion is lowered to [C.sub.2v] on complex formation and six normal modes are expected to be IR active [32]. The compound does not exhibit any strong band ~1380 [cm.sup.-1] but displays two bands, one at 1510 [cm.sup.-1] and another at 1290 [cm.sup.-1] characteristic of [v.sub.1](NO) and [v.sub.4](N[O.sub.2asy]) stretches, respectively, of [C.sub.2v] nitrate group [33], indicating that the nitrate group in the compound is not free ion but is coordinated [34]. The molar conductance data also support this. The bidentate nature of nitrato group is indicated by the presence of bands at 1035 [cm.sup.-1] ([v.sub.2]), 775 [cm.sup.-1] ([v.sub.6]), 750 [cm.sup.-1] ([v.sub.3]), and 690 [cm.sup.-1] ([v.sub.5]) and the combination bands ([v.sub.2] + [v.sub.3]) and ([v.sub.2] + [v.sub.5]) at 1785 and 1735 [cm.sup.-1], respectively. For bidentate coordination of nitrato group [35], the values of ([v.sub.3]-[v.sub.5]) and ([v.sub.1]-[v.sub.4]) are ~38-71 and ~185-235 [cm.sup.-1], respectively; these energy separations lie between 13-20 [cm.sup.-1] and 105-115 [cm.sup.-1] in monodentate nitrato complexes [36]. We have observed the energy separations of these bands as 60 and 220, respectively, indicating the bidentate coordination of nitrato group in the present compound. The new nonligand bands in the present coordination compounds in the low frequency region are assigned to the v(M-O) (545-580 [cm.sup.-1]), the v(M-N) (425-460 [cm.sup.-1]), and the v(M-S) (350-365 [cm.sup.-1]) vibrations 37].

3.2. Reflectance Spectral Studies. [Mn(LH)(MeOH)2] exhibits three bands at 18100, 23200, and 25400 [cm.sup.-1] due to [sup.6][A.sub.1g] [right arrow] [sup.4][T.sub.1g](G), [sup.6][A.sub.1g] [right arrow] [sup.4][T.sub.2g](G), and [sup.6][A.sub.1g] [right arrow] [sup.4][A.sub.1g](G) transitions, respectively, in an octahedral environment [38]. The presence of only one broadband at 16,600 [cm.sup.-1] due to the [sup.2][E.sub.g] [right arrow] [sup.2][T.sub.2g] transitions in [[Cu(LH)].sub.2] suggests a square-planar arrangement of II around Cu(II) ions [39]. The absence of a band in the range 8000-10000 [cm.sup.-1] precludes the presence of a tetrahedral structure [40].

3.3. EPR Studies. The EPR spectrum of [[Cu(LH)].sub.2] in DMSO at 77 K has been recorded in X-band, using 100 kHz field modulation, and the g values are relative to the standard marker tetracyanoethylene (TCNE) (g = 2.0028). The spectrum shows seven hyperfine lines (2nI + 1 = 2 x 2 x (3/2) +1 = 7) in parallel components due to the intramolecular exchange interaction in the dimer with no superhyperfine lines. It exhibits the half-filled line at ~1600 gauss due to [DELTA]Ms = 2 transition and conclusively proves the presence of the magnetic exchange interaction in this coordination compound.

The EPR spectral parameters of [[Cu(LH)].sub.2] are as follows: [g.sub.[parallel]] = 2.25, [g.sub.[perpendicular to]] = 2.07, [A.sub.[parallel]] =92 x [10.sup.-4] [cm.sup.-1], G = 3.65, [[alpha].sup.2.sub.cu] = 0.57, and [g.sub.av] = 2.13. The values of [A.sub.[parallel]], [g.sub.[parallel]], and [g.sub.[perpendicular to]] obtained are close to the values reported for other dimetallic Cu coordination compounds [41]. For ionic environments, [g.sub.[parallel]] is normally [greater than or equal to] 2.3 and is <2.3 for covalent environments. The [g.sub.[parallel]] value (2.25) indicates that the metal-ligand bonding in the compound is covalent. The in-plane covalence parameter ([[alpha].sup.2.sub.cu]) has been calculated using the relation [20]:

[MATHEMATICAL EXPRESSION NOT REPRODUCIBLE IN ASCII], (1)

where [alpha] is related to the overlap integral (S) according to the relation: [[alpha].sup.2] - 2[alpha][alpha]'S + [([alpha]').sup.2] = 1. The smaller the value of [[alpha].sup.2.sub.cu], the more covalent the bonding; [[alpha].sup.2.sub.cu] = 1 indicates complete ionic bonding, while [[alpha].sup.2.sub.cu] = 0.5 indicates complete covalent bonding. On the other hand, the larger the value of [([alpha]').sup.2], the more covalent the bonding; [([alpha]').sup.2] = 0 suggests a complete ionic bonding. The observed value ([[alpha].sup.2.sub.cu]) of [[Cu(LH)].sub.2] is less than unity and this indicates that this compound possesses significant covalent character in the M-L bonding [42].

3.4. Magnetic Measurements. The magnetic moment of [Mn(LH)[(MeOH).sub.2]] is 5.92 B.M. This value is within the normal ranges reported for the magnetically dilute octahedral compounds of Mn(II) ions [43]. The Cu(II) ion belongs to the S = 1/2 system and since its spin-orbit coupling constant is negative [20], the magnetically dilute Cu(II) coordination compound is expected to exhibit magnetic moment higher than the spin-only value of 1.73 B.M. due to the presence of orbital contribution [44]. The magnetic moment (1.55 B.M.) of [[Cu(LH)].sub.2] is substantially less than the above range of magnetic moment and this indicates the presence of antiferromagnetic exchange [20]. The coordination compounds of Cd(II), Zr[(OH).sub.2](IV), and U[O.sub.2](VI) of II are diamagnetic as expected.

3.5. Antibacterial Studies. The antibacterial activities of ligand (II) and its complexes were tested against bacteria, E. coli (Gram negative) and S. aureus (Gram positive), by using disc diffusion method. Stock solution was prepared by dissolving compounds in DMSO. Under aseptic conditions, plain sterilised discs were soaked in solution of compounds for overnight. Test culture was spread over the plates containing Mueller Hinton Agar (MHA) E. coli and S. aureus by using sterile swab. Inoculated plates were dried for 30 minutes and discs were placed on inoculated plates. The plates were left for 30 minutes at room temperature to allow diffusion. The plates were then incubated at 37[degrees]C for 24 hours for E. coli and S. aureus. After incubation, diameter of zone of inhibition was noted for each disc as shown in Table 3.

3.6. Determination of Minimum Inhibitory Concentration (MIC). The stock solution of compounds were prepared using distilled water as diluent. In a set of test tubes having 2 mL of Mueller Hinton Broth, compounds was serially diluted. 2 mL of the test culture was added to all tubes and tubes were incubated at 37[degrees]C for 24 hr. Lack of turbidity was noted for the determination of MIC (Table 4).

4. Conclusions

From the ongoing discussion, it maybe stated that II behaves as a neutral tridentate ONS donor ligand in [Zr[(OH).sub.2] [(OAc).sub.2](L[H.sub.3])], monobasic tridentate ONS donor ligand in [U[O.sub.2](N[O.sub.3])(L[H.sub.2])(MeOH)], dibasic tridentate OOS donor ligand in [[Cu(LH)].sub.2], and dibasic tetradentate OONO donor ligand in [Mn(LH)[(MeOH).sub.2]] and [Cd(LH)].

Thus, on the basis of analytical, molecular weight, spectral, and magnetic studies, we propose a square-planar structure V for [[Cu(LH)].sub.2] a tetrahedral structure, III for [Cd(LH)], an octahedral structure IV for [Mn(LH) [(MeOH).sub.2]], a pentagonal-bipyramidal structure VI for [Zr[(OH).sub.2][(OAc).sub.2](L[H.sub.3])], and an eight-coordinate structure VII for [U[O.sub.2](N[O.sub.3])(L[H.sub.2])(MeOH)] as shown in Figure 3.

Disclosure

This paper is the authors' own work, and the research is original. The results have not been published (in any language or medium), and the paper is not considered and will not be offered elsewhere. Both the authors have read and approved the paper, and due care has been taken to ensure the integrity of the work.

http://dx.doi.org/ 10.1155/2014/286136

Conflict of Interests

No conflict of interests exists in the submission of the paper.

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Dinesh Kumar (1) and Amit Kumar (2)

(1) Department of Chemistry, National Institute of Technology, Kurukshetra, Haryana 136119, India

(2) Department of Chemistry, Haryana College of Technology & Management, Kaithal, Haryana 136027, India

Correspondence should be addressed to Amit Kumar; amit_vashistha2004@yahoo.co.in

Received 29 May 2013; Revised 12 November 2013; Accepted 12 November 2013; Published 4 February 2014

Academic Editor: Liviu Mitu

TABLE 1: Analytical, molar conductance ([[LAMBDA].sub.M]), and
molecular weight data of II and its coordination compounds.

Compound                       Mol. formula        [[LAMBDA].sub.M]
                                                   (mho [cm.sup.2]
                                                    [mol.sup.-1])

L[H.sub.3] (II)            [C.sub.15][H.sub.12]           --
                            [N.sub.2][O.sub.5]
                                [S.sub.2]

[Mn(LH)[(MeOH).sub.2]]    Mn[C.sub.17][H.sub.18]         8.3
                            [N.sub.2][O.sub.7]
                                [S.sub.2]

[[Cu(LH)].sub.2]           [Cu.sub.2][C.sub.30]          5.3
                           [H.sub.20][N.sub.4]
                           [O.sub.10][S.sub.4]

[Cd(LH)]                  Cd[C.sub.15][H.sub.10]         4.6
                            [N.sub.2][O.sub.5]
                                [S.sub.2]

[Zr[(OH).sub.2]           Zr[C.sub.19][H.sub.20]         9.2
  [(OAc).sub.2]            [N.sub.2][O.sub.11]
  (L[H.sub.3])]                 [S.sub.2]

[U[O.sub.2](N[O.sub.3])   U[C.sub.16][H.sub.15]          10.3
  (L[H.sub.2])(MeOH)]      [N.sub.3][O.sub.11]
                                [S.sub.2]

Compound                     Mol. Wt        Obsd (calcd.) %
                          obsd (calcd.)

                                             M         C

L[H.sub.3] (II)             364.0 (a)       --       49.15
                             (364.0)                (49.45)

[Mn(LH)[(MeOH).sub.2]]      458.2 (b)      11.35     42.30
                             (480.9)      (11.42)   (42.42)

[[Cu(LH)].sub.2]            873.0 (b)      14.40     41.80
                             (851.0)      (14.92)   (42.30)

[Cd(LH)]                    490.3 (b)      23.50     37.80
                             (474.4)      (23.69)   (37.94)

[Zr[(OH).sub.2]             638.0 (b)      14.90     37.40

  [(OAc).sub.2]              (607.2)      (15.02)   (37.55)
  (L[H.sub.3])]

[U[O.sub.2](N[O.sub.3])     705.3 (b)      32.63     26.46
  (L[H.sub.2])(MeOH)]        (727.0)      (32.74)   (26.41)

Compound                        Obsd (calcd.) %

                            H        N         S

L[H.sub.3] (II)            3.10     7.50     17.30
                          (3.30)   (7.69)   (17.58)

[Mn(LH)[(MeOH).sub.2]]     3.68     5.76     13.10
                          (3.74)   (5.82)   (13.31)

[[Cu(LH)].sub.2]           2.25     6.50     14.95
                          (2.35)   (6.58)   (15.04)

[Cd(LH)]                   2.00     5.80     13.10
                          (2.11)   (5.90)   (13.49)

[Zr[(OH).sub.2]            3.10     4.46     10.48
  [(OAc).sub.2]           (3.29)   (4.61)   (10.54)
  (L[H.sub.3])]

[U[O.sub.2](N[O.sub.3])    2.11     5.82     8.87
  (L[H.sub.2])(MeOH)]     (2.06)   (5.78)   (8.80)

(a) Mass spectral data, (b) Rast's method data.

TABLE 2: IR, reflectance spectral data ([cm.sup.-]), and magnetic
moments of coordination compounds of II.

Compound                             v(C=O)             v(C-N)
                                (thiazolidinone)   (thiazolidinone)

L[H.sub.3] (II)                       1690               1570
[Mn(LH)[(MeOH).sub.2]]                1690               1515
[[Cu(LH)].sub.2]                      1690               1570
[Cd(LH)]                              1690               1505
[[Zr(OH).sub.2]                       1645               1570
  [(OAc).sub.2](L[H.sub.3])]
[U[0.sub.2](N[O.sub.3])               1660               1570
  (L[H.sub.2])(Me0H)]

Compound                          v(C-O)     [v.sub.as]   [v.sub.s]
                                (phenolic)     (COO)        (COO)

L[H.sub.3] (II)                    1530          --          --
[Mn(LH)[(MeOH).sub.2]]             1540         1565        1347
[[Cu(LH)].sub.2]                   1550         1575        1365
[Cd(LH)]                           1538         1550        1340
[[Zr(OH).sub.2]                    1530          --          --
  [(OAc).sub.2](L[H.sub.3])]
[U[0.sub.2](N[O.sub.3])            1530          --          --
  (L[H.sub.2])(Me0H)]

Compound                        v(C=0)      v(C-S)      v(C-O)
                                (amide)   (thiophene)   (MeOH)

L[H.sub.3] (II)                  1648         640         --
[Mn(LH)[(MeOH).sub.2]]           1628         640        999
[[Cu(LH)].sub.2]                 1648         640         --
[Cd(LH)]                         1613         640         --
[[Zr(OH).sub.2]                  1648         580         --
  [(OAc).sub.2](L[H.sub.3])]
[U[0.sub.2](N[O.sub.3])          1648         595        985
  (L[H.sub.2])(Me0H)]

Compound                            [v.sub.max]       Mag. moment
                                                        (B.M.)

L[H.sub.3] (II)                         --            Diamagnetic
[Mn(LH)[(MeOH).sub.2]]          18100, 23200, 25400      5.92
[[Cu(LH)].sub.2]                       16600             1.55
[Cd(LH)]                                --            Diamagnetic
[[Zr(OH).sub.2]                         --            Diamagnetic
  [(OAc).sub.2](L[H.sub.3])]
[U[0.sub.2](N[O.sub.3])                 --            Diamagnetic
  (L[H.sub.2])(Me0H)]

TABLE 3: Antibacterial activity of ligand (I) and its coordination
compounds (zone of inhibition in mm).

Compound                            E. coli           S. aureus
                                (Gram negative)    (Gram positive)

L[H.sub.3] (II)                        6                  5
[Mn(LH)[(MeOH).sub.2]]                 9                  6
[[Cu(LH)].sub.2]                       8                  10
[Cd(LH)]                               11                 11
[Zr[(OH).sub.2][(OAc).sub.2]           7                  10
  (L[H.sub.3])]
[U[O.sub.2](N[O.sub.3])                10                 12
  (L[H.sub.2])(MeOH)]

TABLE 4: Minimum inhibitory concentration (MIC) of ligand (I) and its
coordination compounds ([micro]g/mL).

Compound                            E. coli           S. aureus
                                (Gram negative)    (Gram positive)

L[H.sub.3] (II)                        32                 64
[Mn(LH)[(MeOH).sub.2]]                 64                 64
[[Cu(LH)].sub.2]                       64                 32
[Cd(LH)]                               64                 64
[Zr[(OH).sub.2]                        32                 32
  [(OAc).sub.2](L[H.sub.3])]
[U[O.sub.2](N[O.sub.3])                32                 64
  (L[H.sub.2])(MeOH)]
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Title Annotation:Research Article
Author:Kumar, Dinesh; Kumar, Amit
Publication:Journal of Chemistry
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Date:Jan 1, 2014
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