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Research ArticleSyntheses Characterization and Biological Activities ofMetal Complexes of N-(2-Carbamoylthienyl)-C-(31015840-carboxy-21015840-hydroxyphenyl) Azetidin-2-one withSome Di- Tetra- and Hexavalent Metal Ions

Dinesh Kumar1 and Amit Kumar2

1 Department of Chemistry National Institute of Technology Kurukshetra Haryana 136119 India2Department of Chemistry Haryana College of Technology amp Management Kaithal Haryana 136027 India

Correspondence should be addressed to Amit Kumar amit vashistha2004yahoocoin

Received 7 May 2013 Revised 14 November 2013 Accepted 14 November 2013 Published 12 February 2014

Academic Editor Peruma Rajakumar

Copyright copy 2014 D Kumar and A Kumar This is an open access article distributed under the Creative Commons AttributionLicense which permits unrestricted use distribution and reproduction in any medium provided the original work is properlycited

The cyclization of the Schiff base N-(2-carbamoylthienyl)-31015840-carboxy-21015840-hydroxybenzylideneimine with ClCH2COCl in diox-

ane in the presence of triethylamine (Et3N) forms N-(2-carbamoylthienyl)-C-(31015840-carboxy-21015840-hydroxyphenyl) azetidin-2-one

LH3(I) A methanolic solution of I reacts with Co(II) Cu(II) Zn(II) Zr(OH)

2(IV) and MoO

2(VI) ions and forms the

coordination compounds [Co(LH)(MeOH)]2(II) [Cu(LH)]

2(III) [Zn(LH)(MeOH)

2] (IV) [Zr(OH)

2(LH)(MeOH)] (V) and

[MoO2(LH)(MeOH)

2] (VI) The compounds have been characterized on the basis of elemental analyses molar conductance

molecularweight spectral (IRNMR reflectance andESR) studies andmagnetic susceptibilitymeasurements All the coordinationcompounds are nonelectrolytes (Λ

119872= 31 minus 92mho cm2 molminus1) in DMF I behaves as a dibasic tridentate OON donor ligand in

V a dibasic tetradentate OONO donor ligand in II III and VI and a dibasic tetradentate OONS donor ligand in IV II andIII are dimers while others are monomers in diphenyl III exhibits subnormal magnetic moment (155 BM) and is involvedin antiferromagnetic exchange while the other complexes are magnetically dilute A square-pyramidal structure for III and anoctahedral structure for II IV and V are suggested VI exhibits an eight-coordinate structure The ligand (I) and its compoundsshow antibacterial activities towards E coli (gram negative) and S aureus (gram positive)

1 Introduction

Azetidinones or 120573-lactams are the 2-carbonyl derivativesof azetidine (a four-membered heterocyclic ring containingN as the heteroatom) These are the most versatile com-pounds used in medicines Antibiotics like cephalosporinsnocardicins and penicillins all possess 120573-lactam ring andtheir biological activities are associated with the chemicalreactivity of the 120573-lactam ring [1]

Azetidinones can be prepared from Schiff rsquos bases whichare the condensation products of aldehydes and amino com-pounds They are considered significant owing to their widerange of biological applications They are also employed asintermediates in chemical synthesis Azetidinones are knownto possess biological and therapeutic activities such as

antibiotic antidepressant sedatives anticancer antibacterialand antipyretic [2ndash5]

Metal ions play a key role in the actions of drugs [6]They are involved in specific interactions with antibioticsproteins membrane components nucleic acids and otherbiomolecules Some transition metals exert pronounced bio-logical effects functioning as active centers within importantbioactive molecules in living systems The introduction of120573-lactam antibiotics into the health care system in the latterstages of World War II represents one of the most importantcontributions to medical science in recent history Today120573-lactams remain the most widely utilized antibiotics owingto their comparatively high effectiveness low cost ease ofdelivery and minimal side effects

Hindawi Publishing CorporationJournal of ChemistryVolume 2014 Article ID 124790 8 pageshttpdxdoiorg1011552014124790

2 Journal of Chemistry

S

O

OH H

C N

Cl C

N

C

O

C

C

O

H

H H

H C

C

O

C

N

O

CCl

NC

H

HOOH

O

S

[I (keto form)] [I (enol form)]

OH

Figure 1

Many drugs possess modified toxicological and pharma-cological properties in the form of metal complexes Tran-sition metal ions possess an important role in the designingof metal-based drugs and such complexes are more effectiveagainst infectious diseases compared to the uncomplexeddrugs The metal which is probably the most widely studiedin this respect is the copper(II) ion which has proved ben-eficial in many diseases such as tuberculosis gastric ulcersrheumatoid arthritis and cancers [7]

These facts motivate us to explore the coordinationbehavior of a newly synthesized azetidin-2-one with transi-tion metal ions

In this report we describe the syntheses and characteri-zation of N-(2-carbamoylthienyl)-C-(31015840-carboxy-21015840-hydroxyphenyl) azetidin-2-one LH

3(I) as shown in Figure 1 and

its coordination compounds with Co(II) Cu(II) Zn(II)Zr(OH)

2(IV) and MoO

2(VI) ions It is expected that the

study of the present azetidinone and its coordination com-pounds may contribute towards the applications in the fieldsof biological and pharmaceutical activities

2 Experimental

21 Materials Copper(II) acetate monohydrate zinc(II)acetate dihydrate (SDrsquos Fine) cobalt(II) acetate tetrahyd-rate hexadecaaquaoctahydroxotetrazirconium(IV) chloride(BDH) ammonium molybdate(VI) tetrahydrate acetyl ace-tone methanol triethylamine chloroacetyl chloride (Ran-baxy) thiophene-2-carboxylic acid hydrazide (Acros Organ-ics (USA)) were used as supplied for the synthesesBis(acetylacetonato)dioxomolybdenum(VI) hexadecaaqua-octahydroxotetrazirconium(IV) acetate and 3-formylsali-cylic acid were synthesized by following the mehods asreported earlier [8]

22 Analyses and Physical Measurements The estimations ofmetal chlorine and the sulphur contents of the respectivecompounds were carried out by the standard methods asreported [9] The C H and N contents were determined bythe Eager analyzer model-300 CHN analyzerThemolar con-ductances of the coordination compounds were determinedin DMSO with the help of a Toshniwal conductivity bridge

(CL01-02A) and a dip type cell calibrated with KCl solutionsThe molecular weights were determined by Rastrsquos methodusing diphenyl as the solvent [10] The IR spectra wererecorded in KBr pellets (4000ndash400 cmminus1) on a Beckman-20spectrophotometer The reflectance spectra were recordedon a Beckmann DU spectrophotometer attached with areflectance arrangement The magnetic susceptibility mea-surements were carried out at room temperature usingHg[Co(NCS)

4] as the standard [11] The diamagnetic correc-

tions were computed using Pascalrsquos constants The magneticsusceptibilities were corrected for temperature independentparamagnetism term (TIP)11 using value of 200 times 10minus6cgsunits for Co(II) and 60 times 10minus6cgs units for Cu(II) ions

23 Synthesis of N-(2-Carbamoylthienyl)-31015840 -carboxy-21015840-hydroxybenzylideneimine (Schiff Base) A MeOH solution(30mL) of thiophene-2-carboxylic acid hydrazide (142 g10mmol) was added to a MeOH solution (30mL) of 3-formylsalicylic acid (166 g 10mmol) The mixture wasrefluxed for 2 h and the precipitates formed were suction-filtered washed with and recrystallized from MeOH anddried in vacuo at room temperature over silica gel for 24 hYield was 80The elemental analyses of the title compoundgave the satisfactory results

24 Synthesis of N-(2-Carbamoylthienyl)-C-(31015840 -carboxy-21015840 -hydroxyphenyl) Azetidin-2-one (I) The title compound wassynthesized by the drop-wise addition of chloroacetylchloride (226 g 20mmol) during a period of 2 h to adioxane solution (50mL) of the Schiff base (290 g 10mmol)in the presence of triethylamine (303 g 30mmol) whilestirring constantly Triethylamine hydrochloride formedwas filtered off and the volume of the filtrate was reducedto 50 The solution was kept aside for 24 h and the solidproduct formed was suction-filtered washed with dioxaneand recrystallized from CHCl

3 The compound was dried as

mentioned above Yield = 28 Anal (I C15H11N2O5SCl)

(obsd C 4880 H 288 N 750 S 850 Cl 948calc C 4911 H 300 N 764 S 873 Cl 969)IR bands (KBr) 2900 cmminus1 [](OndashH)(intramolecular H-bonded)] 1750 cmminus1 [](C=O)(120573-lactam)] 1660 cmminus1

Journal of Chemistry 3

Table 1 Analytical molar conductance (Λ119872) and molecular weight data of I and its coordination compounds

Compound Mol formula Λ119872

(mho cm2 molminus1)Mol Wt obsd

(calcd)Obsd (calcd)

M C H N S Cl

LH3 (I) C15H11N2O5SCl mdash 365a(3665) mdash 4880

(4911)288(300)

750(764)

850(873)

948(969)

[Co(LH)(MeOH)]2 Co2C32H26N4O12S2Cl2 31 8873b(9108)

1260(1293)

4200(4216)

292(286)

590(615)

688(703)

765(780)

[Cu(LH)]2 Cu2C30H18N4O10S2Cl2 90 8745b(8560)

1470(1484)

4186(4206)

200(210)

640(654)

728(748)

815(829)

[Zn(LH)(MeOH)2] ZnC17H17N2O7SCl 73 4622b(4939)

1320(1324)

4126(4130)

340(344)

562(567)

642(648)

714(719)

[Zr(OH)2(LH)(MeOH)] ZrC16H15N2O8SCl 63 5475b(5217)

1774(1748)

3675(3680)

284(288)

534(537)

609(613)

675(680)

[MoO2(LH)(MeOH)2] MoC17H17N2O9SCl 92 5728b(5564)

1720(1724)

3662(3666)

300(306)

498(503)

570(575)

632(638)

aMass spectral data bRast method data

Schiff baseChloroacetyl chloride

LH3Triethylamine dioxane(I)

Scheme 1 Preparative scheme of LH3(I)

[](C=O)(amide)] 1536 cmminus1 [](CndashO)(phenolic)] 1414 cmminus1[](CndashN)(120573-lactam)] 748 cmminus1 [](CndashCl)(120573-lactam)] and 645[](CndashS)(thiophene)]

25 Syntheses of Coordination Compounds of I A MeOHsolution (30ndash50mL) of the appropriate metal salt (10mmol)was added to aMeOH solution (50mL) of I (366 g 10mmol)and the mixture was then refluxed for 3-4 h The solidproducts formed were suction-filtered washed with MeOHand then dried as mentioned above Yield was 55ndash75

3 Results and Discussion

N-(2-Carbamoylthienyl)-C-(31015840-carboxy-21015840-hydroxyphenyl)azetidin-2-one LH3 (I) was synthesized by the reactionof chloroacetyl chloride on the Schiff base N-(2-carbam-oylthienyl)-31015840-carboxy-21015840-hydroxybenzylideneimine Thereaction of I with appropriate metal salts in 1 1 molar ratioin MeOH produces the coordination compounds of thetypes [Co(LH)(MeOH)]

2 [Cu(LH)]

2 [Zn(LH)(MeOH)

2]

[Zr(OH)2(LH)(MeOH)] and [MoO

2(LH)(MeOH)

2] The

coordination compounds are insoluble in H2O MeOH and

EtOH They are partially soluble in CHCl3 Me2CO and

C6H6and completely soluble in DMSO and DMF They are

nonelectrolytes (Λ119872= 31ndash92mho cm2molminus1) in DMF

The analytical data of I and its coordination compounds aregiven in Table 1 The formation of coordination compoundsof I takes place according to Schemes 1 and 2

31 Infrared Spectral Studies The infrared spectra of theSchiff base I and its coordination compounds were recordedin KBr pellets and the prominent peaks (in cmminus1) areshown in Table 2 The conversion of the Schiff base to

the corresponding azetidinone is confirmed by the disappear-ance of the ](C=N)(azomethine) stretch occurring originallyat 1625 cmminus1 in the former and the appearance of a new bandat 1414 cmminus1 due to the ](CndashN)(120573-lactam) stretch [12] in thelatter The formation of I is further supported by the appear-ance of a new band at 748 cmminus1 due to the ](CndashCl)(120573-lactam)stretch [13] in its IR spectrum I exhibits a strong band at2900 cmminus1 due to the intramolecular H-bonded OH groupof phenolic andor carboxylic acid moieties [14] This banddisappears in the coordination compounds indicating thebreakdown of H-bonding and subsequent deprotonation ofthe OH groups followed by the involvement of phenolic andcarboxylic acid O atoms towards coordination The presenceof a broad band between 3350 and 3450 cmminus1 due to the ](OndashH)(MeOH) stretch and the decrease of the ](CndashO)(MeOH)stretch from 1034 cmminus1 to lower energy by 49ndash74 cmminus1 inthe coordination compounds of Co(II) Zn(II) Zr(OH)

2(IV)

and MoO2(VI) ions indicate the involvement of the O atom

of MeOH towards coordination [15] I occurs in the keto-form as evident by the presence of a strong band due tothe ](C=O)(amide) stretch at 1660 cmminus1 This band remainsat the same energy in the coordination compounds IVand V indicating the noninvolvement of the keto O atomtowards coordination However this band shifts to lowerenergy by 25 cmminus1 in [Cu(LH)]

2indicating the involvement

of the keto O atom towards coordination II and VI donot display ](C=O)(amide) stretch but show a new band at1255 and 1240 cmminus1 respectively suggesting the conversionof ndashC(O)NHndash moiety (keto-form) into ndashC (OH)=Nndash moiety(enol-form) followed by the involvement of enolic O atomtowards coordination

The ](CndashN)(120573-lactam) stretch of I shifts from 1414 cmminus1to lower energy by 24ndash39 cmminus1 in the complexes indicating


RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH

LH3 + Zn(CH3COO)2 middot 2H2O

2LH3 + 2Co(CH3COO)2 middot 4H2O

4LH3 + [Zr4(OH)8(H2O)16](CH3COO)8

LH3 + [MoO2(acac)2]

[Cu(LH)]2 + 4CH3COOH + 2H2O

[Zn(LH)(MeOH)2] + 2CH3COOH + 2H2O

[Co(LH)(MeOH)]2 + 4CH3COOH + 8H2O

4[Zr(OH)2(LH)(MeOH) + 8CH3COOH + 16H2O

[MoO2(LH)(MeOH)2] + 2acacH

2LH3 + 2Cu(CH 3COO)2 middot H2O

Scheme 2 Preparative scheme of coordination compounds of LH3(I)

Table 2 IR reflectance spectral data (cmminus1) and magnetic moments of coordination compounds of I

Compound ]as(COO) ]119904(COO) ](CndashO)

(phenolic)](CndashN)

(120573-lactam)](C=O)(amide)

](CndashO)(enolic)

](CndashO)(MeOH) ]max

Magmoment(BM)

LH3 (I) mdash mdash 1536 1414 1660 mdash mdash mdash Diamagnetic

[Co(LH)(MeOH)]2 1580 1365 1556 1385 mdash 1255 97592601322019280

486

[Cu(LH)]2 1580 1350 1565 1375 1635 mdash mdash 18100 155[Zn(LH)(MeOH)2] 1580 1375 1544 1390 1660 mdash 960 mdash Diamagnetic[Zr(OH)2(LH)(MeOH)] 1555 1350 1546 1385 1660 mdash 985 mdash Diamagnetic[MoO2(LH)(MeOH)2] 1570 1355 1545 1382 mdash 1240 965 mdash Diamagnetic

the involvement of the N atom of 120573-lactam moiety towardscoordination [16] The ](C=O)(120573-lactam) stretch [17] of Ioccurring at 1750 cmminus1 remains unchanged in the coor-dination compounds suggesting the noninvolvement ofthe O atom of 120573-lactam moiety towards coordination Theappearance of two new bands between 1555 and 1580 cmminus1and between 1350 and 1375 cmminus1 assignable to the ]as(COO)and ]119904(COO) stretches respectively of the carboxylate group

with an energy difference of 205ndash230 cmminus1 indicates themonodentate nature of the carboxylate moiety [18] The](CndashO)(phenolic) stretch [19] of I occurring at 1536 cmminus1shifts to higher energy by le10 cmminus1 in the IV V and VIwhile it shifts by 20 and 29 cmminus1 in II and III respectivelysupporting the involvement of phenolic O atom towardscoordination The Cl atom of 120573-lactam moiety does not takepart in coordination as evident by the occurrence of the ](CndashCl)(120573-lactam) stretch [13] (748 cmminus1) of I unaltered in thecoordination compounds

The ](CndashS)(thiophene) stretch [20] of the ligand shiftsfrom 645 cmminus1 to lower energy by 50 cmminus1 in IV whileit remains unchanged in the rest of the compounds Theabsence of a band in the region 835ndash955 cmminus1 due to the](Zr=O) stretch [21] in the present Zr(OH)

2(IV) compound

suggests its formulation as [Zr(OH)2(LH)(MeOH)] and not

as [ZrO(H2O)(LH)(MeOH)]Thepresence of a broad band at

3450 cmminus1 due to the coordinated OH group of H2O andor

MeOH and the appearance of a new medium intense band at

1135 cmminus1 due to the 120575(ZrndashOH) bending mode [22] also sup-port the proposed structure V of the present Zr(OH)

2(IV)

compoundVI exhibits the ]119904(O=Mo=O) and ]as(O=Mo=O)

stretches at 950 and 918 cmminus1 respectively [22] Thesebands occur in the usual ranges ]

119904(O=Mo=O) stretch

892ndash964 cmminus1 and ]as(O=Mo=O) stretch 842ndash928 cmminus1 reported for the majority of MoO

2(VI) compounds [22]

The presence of two bands due to the ](O=Mo=O) stretchis indicative of a cis-MoO

2configuration as the complex

with trans-MoO2structure shows only ]as(O=Mo=O) stretch

since the ]119904(O=Mo=O) stretch is IR inactive [23] The

cis-structure VI forces the tetradentate ligand to coordinatein a nonplanar fashion [24] The absence of a band atsim775 cmminus1 in the present compound indicates the absence ofan oligomeric chain with sdot sdot sdotMo sdot sdot sdotMo sdot sdot sdotMo sdot sdot sdot interaction[24] The new nonligand bands in the present coordinationcompounds in the low frequency region are assigned to the](MndashO) (550ndash575 cmminus1) the ](MndashN) (430ndash460 cmminus1) andthe ](MndashS) (330 cmminus1) stretches These bands are in theexpected order of increasing energy ](MndashS) lt ](MndashN) lt](MndashO) [25]

32 NMR Spectral Studies The NMR spectra of LH3(I) and

[Zn(LH)(MeOH)2] were recorded in DMSO-119889

6 The chem-

ical shifts (120575) are expressed in ppm downfield from TMSThe prominent resonance signals of these compounds werecompared with the reported peaks [26] I exhibits a singletat 120575 177 ppm due to the carboxylic proton a sharp singlet at


120575 1363 ppm due to phenolic proton a singlet at 120575 106 ppm(due to CONH proton) and at 112 ppm (due to HO-C=Ntautomeric protons) and multiplets between 120575 734ndash770 ppmdue to the aromatic protons The absence of the signal at120575 175 ppm due to the COOH proton in [Zn(LH)(MeOH)

2]

indicates the deprotonation of the COOH group followed bythe involvement of its O atom in coordination The absenceof the resonance signal at 120575 1360 ppm due to the phenolicproton in [Zn(LH)(MeOH)

2] indicates the deprotonation

of the phenolic OH group followed by its involvement incoordination [27] The singlet at 120575 104 ppm due to CONHproton remains unchanged in the complex and shows itsnoninvolvement in the coordination The appearance ofresonance signals at 282 ppm due to alcoholic proton andat 30-31 ppm due to methyl protons in the coordinationcompound supports the presence of MeOH in it

33 Reflectance Spectral Studies Due to the poor solubilityof the coordination compounds in commonnoncoordinatingorganic solvents their solution electronic spectra couldnot be recorded and hence the reflectance spectra wererecorded (Table 2) II exhibits three bands at 9260 13220and 19280 cmminus1 due to 4T

1 119892(F) rarr 4T

2 119892(]1) 4T1 119892(F) rarr

4A2 119892(]2) and 4T

1 119892(F) rarr 4T

1 119892(]3) transitions respectively

suggesting an octahedral arrangement of LH3around Co(II)

ions [28] The ]3]1value is 208 which lies in the usual

range (200ndash280) reported for the majority of octahedralCo(II) compounds [28] The spectral parameters [29] are119863119902 = 1040 cmminus1 1198611015840 = 744 cmminus1 120573 = 1198611015840119861 = 077 1205730 =23 and CFSE = minus9937 kJmolminus1 The reduction of Racahparameter from the free ion value of 971 cmminus1 to 744 cmminus1and the 1205730 value (23) indicates the covalent nature of thecompound and the strong field nature of the tetradentateligand [11] The presence of a shoulder at 18100 cmminus1 due tothe dminusd transitions in [Cu(LH)]

2suggests a square-pyramidal

arrangement of LH3around Cu(II) ions [30]

34 ESR Studies The ESR spectrum of [Cu(LH)]2in DMSO

at 77K has been recorded in X-band using 100 kHz fieldmodulation and the 119892 values are relative to the standardmarker tetracyanoethylene (TCNE) (119892 = 20028) Thespectrum shows seven hyperfine lines (2 119899119868+1 = 2times2times(32)+1 = 7) in parallel components due to the intramolecularexchange interaction in the dimer with no superhyperfinelines It exhibits the half-filled line at sim1600 gauss due toΔ119872119904 = 2 transition and conclusively proves the presenceof the magnetic exchange interaction in this coordinationcompound

The ESR spectral parameters of [Cu(LH)]2are as follows

119892= 226 119892

perp= 207 119860

= 90 times 10

minus4 cmminus1 119866 = 379 1205722Cu =058 (1205721015840)2 = 050 and119892av = 213The values of119860

119892 and119892

perp

obtained are close to the values reported for other dimetallicCu coordination compounds [31] For ionic environments119892is normally ge23 and is lt23 for covalent environments

The 119892value (226) indicates that themetal-ligand bonding in

Table 3 Antibacterial activity of ligand (I) and its coordinationcompounds (zone of inhibition in mm)

Compound E coli(gram negative)

S aureus(gram positive)

LH3 (I) 5 4[Co(LH)(MeOH)]2 7 6[Cu(LH)]2 8 7[Zn(LH)(MeOH)2] 9 6[Zr(OH)2(LH)(MeOH)] 7 6[MoO2(LH)(MeOH)2] 10 8

the compound is covalent The in-plane covalence parameter(1205722Cu) has been calculated using the relation [11]

1205722

Cu = (119892 minus 2002) + 37 (119892perp minus 2002) minus (1198600036) + 004

(1)

where 120572 is related to the overlap integral (119878) according to therelation 1205722 minus 21205721205721015840119878 + (1205721015840)2 = 1 The smaller the value of 1205722Cuthe more covalent the bonding 1205722Cu = 1 indicates completeionic bonding while 1205722Cu = 05 indicates complete covalentbonding On the other hand the larger the value of (1205721015840)2 themore covalent the bonding (1205721015840)2 = 0 suggests a completeionic bonding The observed value (1205722Cu) of [Cu(LH)]

2is less

than unity and this indicates that this compound possessessignificant covalent character in the M-L bonding [27]

35 Magnetic Measurements The room temperature mag-netic moments of the compounds are presented in Table 2Themagnetic moment of II is 486 BMThis value lies in theusual ranges reported for the majority of octahedral Co(II)coordination compounds [32] The Cu(II) ion belongs to the119878 = 12 system and since its spin-orbit coupling constantis negative [11] due to the presence of orbital contributionthe magnetically dilute Cu(II) compound is expected toexhibit magnetic moment higher than the spin-only value(173 BM) [11] The magnetic moment (155 BM) of III issubstantially less than the above range of magnetic momentand this indicates the presence of antiferromagnetic exchangeinteraction [11] IV V and VI are diamagnetic in nature

36 Antibacterial Studies The antibacterial activity of ligand(I) and its complexes were tested against bacteria E coli(gram negative) and S aureus (gram positive) by using discdiffusion method (as shown in Table 3) Stock solution wereprepared by dissolving compounds in DMSO Under asepticconditions plain sterilised discs were soaked in solution ofcompounds for overnight Test culture was spread over theplates containing Mueller Hinton Agar (MHA) E coli and Saureus by using sterile swab Inoculated plates were dried for30 minutes and discs were placed on inoculated plates Theplates were left for 30 minutes at room temperature to allowdiffusionTheplates were then incubated at 37∘C for 24 hoursAfter incubation diameter of zone of inhibitionwas noted foreach disc


N

C

H

O

O

O

O

CC

H

O

C

C

Cl

SCo Co

N

N

S

Cl

C

C

O

H

CC

O

O

O

O

HC

N

H

H

A

A

[II A = MeOH]

S

H

Cu Cu

O

O

O

H

H Cl

C C

C

C

CS

N

NO

O

HC

C

OO

N

O

O

Cl

H

CN

H

C C

O

[III]

A

AN

O

C

O

O

C

S

O

ClC

HN

OH

C

CH Zn

[IV A = MeOH]

HO

A

N CC

H

NCH

Cl

C

OO

SOH

C

O

O

OZr

H

[V A = MeOH]

O

S

O

H

C

C

OH

O

N

Mo

O

OCl

CNC

C

O

A AH

[VI A = MeOH]

Figure 2

Table 4 Minimum inhibitory concentration (MIC) of ligand (I)and its coordination compounds (120583gmL)




37 Determination of Minimum Inhibitory Concentration(MIC) The stock solution of compounds was prepared usingDMSO as diluent In a set of test tubes having 2mL ofMuellerHintonBroth compoundswere serially diluted 2mLof the test culture was added to all tubes and tubes wereincubated at 37∘C for 24 hr Lack of turbidity was noted forthe determination of MIC (Table 4)

4 Conclusion

On the basis of analytical data molecular weight valencerequirements and spectral and magnetic studies it is

proposed that I behaves as a dibasic tridentate OON donorligand inmonomeric six-coordinate diamagnetic octahedralcompound [Zr(OH)

2(LH)(MeOH)] (V) a dibasic tetraden-

tate OONO donor ligand in dimeric six-coordinatehigh-spin octahedral compound [Co(LH)(MeOH)]

2(II)

dimeric five-coordinate square-pyramidal compound[Cu(LH)]

2(III) monomeric eight-coordinate compound

[MoO2(LH)(MeOH)

2] (VI) and a dibasic tetradentate

OONS donor ligand in diamagnetic six-coordinateoctahedral compound [Zn(LH)(MeOH)

2] (IV) as shown in

Figure 2

Disclosure

This paper is the authorsrsquo own work and the research isoriginalThe results have not been published (in any languageor medium) and the paper is not considered and will not beoffered elsewhere Both the authors have read and approvedthe paper and due care has been taken to ensure the integrityof the work

Conflict of Interests

No conflict of interests exists in the submission of the paper


Acknowledgment

One of the authors (Dr Amit Kumar) is grateful to the Direc-tor of his institute for financial assistance and encouragementfor this work

References

[1] E G Mata M Fraga and C M L Delpiccolo ldquoAn efficientstereoselective solid-phase synthesis of 120573-lactams usingMukai-yamarsquos salt for the staudinger reactionrdquo Journal of CombinatorialChemistry vol 5 no 3 pp 208ndash210 2003

[2] D Sharma P Kumar and B Narasimhan ldquoSynthesis and anti-bacterial evaluation of Cu(II) and Zn(II) complexes of the 120573-lactum antibiotic cefdinirrdquo Medicinal Chemistry Research vol21 no 6 pp 796ndash803 2012

[3] F H Havaldar and S K J Mishra ldquoSynthesis of some aze-tidin-2-ones and thiazolidin-4-ones as potential antimicrobialagentsrdquo Indian Journal of Heterocyclic Chemistry vol 13 no 3pp 197ndash200 2004

[4] J R Anacona and J Serrano ldquoSynthesis and antibacterial activ-ity of metal complexes of cephalothinrdquo Journal of CoordinationChemistry vol 56 no 4 pp 313ndash320 2003

[5] M N Kumaraswamy V P Vaidya C Chandrasekhar D APrathima Mathias H Shivakumar and K M MahadevanldquoSynthesis and pharmacological investigations of azetidinonederivatives involving naphtho[21-b]furan-2-carboxamiderdquoResearch Journal of Pharmaceutical Biological and ChemicalSciences vol 4 no 1 p 90 2013

[6] J R Anacona and H Rodriguez ldquoMetalloantibiotics synthesisand antibacterial activity of cefepime metal complexesrdquo Journalof Coordination Chemistry vol 62 no 13 pp 2212ndash2219 2009

[7] D H Brown W E Smith J W Teape and A J Lewis ldquoAnti-inflammatory effects of some copper complexesrdquo Journal ofMedicinal Chemistry vol 23 no 7 pp 729ndash734 1980

[8] D Kumar A Syamal A Kumar P K Gupta and D DassldquoSyntheses and characterization of coordination compoundsof N-(2-mercaptoethyl)-4-(31015840-carboxy-21015840-hydroxyphenyl)-2-azetidinonerdquo Journal of the Indian Chemical Society vol 87 no4 pp 417ndash423 2010

[9] A I Vogel A Textbook of Quantitative Inorganic Analysis ELBSand Longman London UK 1978

[10] F G Mann and B C Saunders Practical Organic ChemistryLongmans London UK 1961

[11] R L Dutta and A Syamal Elements of MagnetochemistryAffiliated East West Press New Delhi India 2nd edition 1993

[12] Z H Chohan and C T Supuran ldquoMetalloantibiotics synthesischaracterization and in-vitro antibacterial studies on cobalt (II)copper (II) nickel (II) and zinc (II) complexes with cloxacillinrdquoJournal of Enzyme Inhibition and Medicinal Chemistry vol 21no 4 pp 441ndash448 2006

[13] E Jayachandran L V G Nargund A Roy G M Sreenivasaand K Krupanidhi ldquoSynhesis of 1-[6rsquo-fluoro-7rsquo substituted-(13rsquo) benzothiazol-2-yl] amino-4-substituted-3 chloro azeti-din-2-one for antimicrobial screeningrdquo Oriental Journal ofChemistry vol 23 no 3 pp 829ndash835 2007

[14] P J Bahad N S Bhave and A S Aswar ldquoSynthesis structuraland electrical studies of cobalt- nickel- copper- and zinc(II)polymeric complexesrdquo Journal of the Indian Chemical Societyvol 77 no 8 pp 363ndash366 2000

[15] D Kumar A Syamal A Kumar D Dass and A Gupta ldquoSpec-tral studies on metal complexes of a newly synthesized azetidi-nonerdquo Asian Journal of Chemistry vol 21 no 9 pp 7345ndash73532009

[16] Z H Chohan C T Supuran and A Scozzafava ldquoMetal-loantibiotics synthesis and antibacterial activity of cobalt(II)copper(II) nickel(II) and zinc(II) complexes of kefzolrdquo Journalof Enzyme Inhibition and Medicinal Chemistry vol 19 no 1 pp79ndash84 2004

[17] J R Anacona and M Lopez ldquoMixed-ligand nickel(II) com-plexes containing sulfathiazole and cephalosporin antibioticssynthesis characterization and antibacterial activityrdquo Interna-tional Journal of Inorganic Chemistry vol 2012 Article ID106187 8 pages 2012

[18] K Nakamoto Infrared and Raman Spectra of Inorganic andCoordination Compounds JohnWiley New York NY USA 4thedition 1986

[19] D Kumar A Kumar and J Sharma ldquoPhysico-chemical studieson the coordination compounds of thiazolidin-4-onerdquo Journalof Chemistry vol 2013 Article ID 870325 7 pages 2013

[20] D Kumar and A Kumar ldquoSyntheses magnetic and spectralstudies on the coordination compounds of the polystyrene-anchored thiazolidin-4-onerdquo E-Journal of Chemistry vol 9 no4 pp 2532ndash2539 2012

[21] D Kumar A Kumar and D Dass ldquoSyntheses and charac-terization of the coordination compounds of N-(2-hydrox-ymethylphenyl)-C-(31015840-carboxy-21015840-hydroxyphenyl)thiazolidin-4-onerdquo International Journal of Inorganic Chemistry vol 2013Article ID 524179 6 pages 2013

[22] D Kumar A Syamal Jaipal and L K Sharma ldquoSynthesis mag-netic and spectral studies on polystyrene-anchored coordina-tion complexes of bi- tri- tetra- and hexavalent metal ions withunsymmetrical dibasic tetradentate ONNO donor Schiff basederived from 3-formylsalicylic acid ethylenediamine and 2-benzoylacetaniliderdquo Journal of Chemical Sciences vol 121 no1 pp 57ndash64 2009

[23] A Syamal and M R Maurya ldquoDioxomolybdenum(VI) com-plexes with tridentate dibasic Schiff bases derived from varioushydrazidesrdquo Transition Metal Chemistry vol 11 no 6 pp 235ndash238 1986

[24] K Dey B K Maity and J K Bhar ldquoOxocation complexes PartX Oxomolybdenum(V) and dioxomolybdenum(VI) com-plexes with tri- and tetra-dentate Schiff basesrdquo Transition MetalChemistry vol 6 no 6 pp 346ndash351 1981

[25] J R Ferraro Low Frequency Vibrations of Inorganic and Coordi-nation Compounds Plenum Press New York NY USA 1971

[26] B J K Nag S Pal and C Sinha ldquoSynthesis and character-ization of cobalt(II) nickel(II) copper(II) palladium(II) anddioxouranium(VI) complexes of the antipyrine Schiff base of3-formylsalicylic acidrdquo Transition Metal Chemistry vol 30 no5 pp 523ndash526 2005

[27] D Kumar A Syamal A Gupta M Rani and P K Gupta ldquoRoleof pHon the formation of the coordination compoundswith theSchiff base derived from 3-formylsalicylic acid and 4-amino-23-dimethyl-1-phenyl-3-pyrazolin-5-onerdquo Journal of the IndianChemical Society vol 87 no 10 pp 1185ndash1197 2010

[28] A B P Lever Inorganic Electronic Spectroscopy Elsevier Ams-terdam The Netherlands 2nd edition 1984

[29] J E Huheey Inorganic Chemistry Principles of Structure andReactivity Harper and Row New York NY USA 3rd edition1983


[30] M Todokora H Saiyama N Matsumoto M Kodeva HOkawa and S Kida ldquoTemplate synthesis of copper(II)lead(II)complexes of new binucleating macrocycles with dissimilarco-ordination sitesrdquo Journal of the Chemical Society DaltonTransactions no 2 pp 313ndash317 1992

[31] P Athappan S Sevagapandian and G Rajgopal ldquoSynthesisand spectral studies of copper(II) nickel(II) cobalt(II) andvanadyl(II) complexes of tridentate Schiff bases of 12356788a-octahydro-3-oxo-N1-diphenyl-5-(phenylmethylene)-2-naphthalenecarboxamide rdquo Transition Metal Chemistry vol20 no 5 pp 472ndash476 1995

[32] F Cotton A G Wilkinson C Murillo and M BochmannAdvanced Inorganic Chemistry JohnWileyNewYorkNYUSA6th edition 1999

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy


Carbohydrate Chemistry

International Journal of


Journal of

Chemistry


Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of


The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of


Chromatography Research International


Applied ChemistryJournal of



Theoretical ChemistryJournal of


Journal of

Spectroscopy

Analytical ChemistryInternational Journal of


Journal of


Quantum Chemistry


Organic Chemistry International

ElectrochemistryInternational Journal of



CatalystsJournal of


S

O

OH H

C N

Cl C

N

C

O

C

C

O

H

H H

H C

C

O

C

N

O

CCl

NC

H

HOOH

O

S

[I (keto form)] [I (enol form)]

OH

Figure 1

Many drugs possess modified toxicological and pharma-cological properties in the form of metal complexes Tran-sition metal ions possess an important role in the designingof metal-based drugs and such complexes are more effectiveagainst infectious diseases compared to the uncomplexeddrugs The metal which is probably the most widely studiedin this respect is the copper(II) ion which has proved ben-eficial in many diseases such as tuberculosis gastric ulcersrheumatoid arthritis and cancers [7]

These facts motivate us to explore the coordinationbehavior of a newly synthesized azetidin-2-one with transi-tion metal ions

In this report we describe the syntheses and characteri-zation of N-(2-carbamoylthienyl)-C-(31015840-carboxy-21015840-hydroxyphenyl) azetidin-2-one LH

3(I) as shown in Figure 1 and

its coordination compounds with Co(II) Cu(II) Zn(II)Zr(OH)

2(IV) and MoO

2(VI) ions It is expected that the

study of the present azetidinone and its coordination com-pounds may contribute towards the applications in the fieldsof biological and pharmaceutical activities

2 Experimental

21 Materials Copper(II) acetate monohydrate zinc(II)acetate dihydrate (SDrsquos Fine) cobalt(II) acetate tetrahyd-rate hexadecaaquaoctahydroxotetrazirconium(IV) chloride(BDH) ammonium molybdate(VI) tetrahydrate acetyl ace-tone methanol triethylamine chloroacetyl chloride (Ran-baxy) thiophene-2-carboxylic acid hydrazide (Acros Organ-ics (USA)) were used as supplied for the synthesesBis(acetylacetonato)dioxomolybdenum(VI) hexadecaaqua-octahydroxotetrazirconium(IV) acetate and 3-formylsali-cylic acid were synthesized by following the mehods asreported earlier [8]

22 Analyses and Physical Measurements The estimations ofmetal chlorine and the sulphur contents of the respectivecompounds were carried out by the standard methods asreported [9] The C H and N contents were determined bythe Eager analyzer model-300 CHN analyzerThemolar con-ductances of the coordination compounds were determinedin DMSO with the help of a Toshniwal conductivity bridge

(CL01-02A) and a dip type cell calibrated with KCl solutionsThe molecular weights were determined by Rastrsquos methodusing diphenyl as the solvent [10] The IR spectra wererecorded in KBr pellets (4000ndash400 cmminus1) on a Beckman-20spectrophotometer The reflectance spectra were recordedon a Beckmann DU spectrophotometer attached with areflectance arrangement The magnetic susceptibility mea-surements were carried out at room temperature usingHg[Co(NCS)

4] as the standard [11] The diamagnetic correc-

tions were computed using Pascalrsquos constants The magneticsusceptibilities were corrected for temperature independentparamagnetism term (TIP)11 using value of 200 times 10minus6cgsunits for Co(II) and 60 times 10minus6cgs units for Cu(II) ions

23 Synthesis of N-(2-Carbamoylthienyl)-31015840 -carboxy-21015840-hydroxybenzylideneimine (Schiff Base) A MeOH solution(30mL) of thiophene-2-carboxylic acid hydrazide (142 g10mmol) was added to a MeOH solution (30mL) of 3-formylsalicylic acid (166 g 10mmol) The mixture wasrefluxed for 2 h and the precipitates formed were suction-filtered washed with and recrystallized from MeOH anddried in vacuo at room temperature over silica gel for 24 hYield was 80The elemental analyses of the title compoundgave the satisfactory results

24 Synthesis of N-(2-Carbamoylthienyl)-C-(31015840 -carboxy-21015840 -hydroxyphenyl) Azetidin-2-one (I) The title compound wassynthesized by the drop-wise addition of chloroacetylchloride (226 g 20mmol) during a period of 2 h to adioxane solution (50mL) of the Schiff base (290 g 10mmol)in the presence of triethylamine (303 g 30mmol) whilestirring constantly Triethylamine hydrochloride formedwas filtered off and the volume of the filtrate was reducedto 50 The solution was kept aside for 24 h and the solidproduct formed was suction-filtered washed with dioxaneand recrystallized from CHCl

3 The compound was dried as

mentioned above Yield = 28 Anal (I C15H11N2O5SCl)

(obsd C 4880 H 288 N 750 S 850 Cl 948calc C 4911 H 300 N 764 S 873 Cl 969)IR bands (KBr) 2900 cmminus1 [](OndashH)(intramolecular H-bonded)] 1750 cmminus1 [](C=O)(120573-lactam)] 1660 cmminus1





(calcd)Obsd (calcd)

M C H N S Cl


(4911)288(300)

750(764)

850(873)

948(969)


1260(1293)

4200(4216)

292(286)

590(615)

688(703)

765(780)

[Cu(LH)]2 Cu2C30H18N4O10S2Cl2 90 8745b(8560)

1470(1484)

4186(4206)

200(210)

640(654)

728(748)

815(829)


1320(1324)

4126(4130)

340(344)

562(567)

642(648)

714(719)


1774(1748)

3675(3680)

284(288)

534(537)

609(613)

675(680)


1720(1724)

3662(3666)

300(306)

498(503)

570(575)

632(638)









2 [Cu(LH)]

2 [Zn(LH)(MeOH)

2]


2(LH)(MeOH)

2] The








2(IV)







RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH



4LH3 + [Zr4(OH)8(H2O)16](CH3COO)8

LH3 + [MoO2(acac)2]












](CndashO)(enolic)


Magmoment(BM)


[Co(LH)(MeOH)]2 1580 1365 1556 1385 mdash 1255 97592601322019280

486





2(IV) compound






2(IV)













6 The chem-




2]





1 119892(F) rarr 4T

2 119892(]1) 4T1 119892(F) rarr

4A2 119892(]2) and 4T

1 119892(F) rarr 4T










119892= 226 119892

perp= 207 119860

= 90 times 10


119892 and119892

perp








1205722


(1)


2is less





N

C

H

O

O

O

O

CC

H

O

C

C

Cl

SCo Co

N

N

S

Cl

C

C

O

H

CC

O

O

O

O

HC

N

H

H

A

A

[II A = MeOH]

S

H

Cu Cu

O

O

O

H

H Cl

C C

C

C

CS

N

NO

O

HC

C

OO

N

O

O

Cl

H

CN

H

C C

O

[III]

A

AN

O

C

O

O

C

S

O

ClC

HN

OH

C

CH Zn

[IV A = MeOH]

HO

A

N CC

H

NCH

Cl

C

OO

SOH

C

O

O

OZr

H

[V A = MeOH]

O

S

O

H

C

C

OH

O

N

Mo

O

OCl

CNC

C

O

A AH

[VI A = MeOH]

Figure 2






4 Conclusion





2(II)



[MoO2(LH)(MeOH)



2] (IV) as shown in

Figure 2

Disclosure





Acknowledgment


References











































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of





(calcd)Obsd (calcd)

M C H N S Cl


(4911)288(300)

750(764)

850(873)

948(969)


1260(1293)

4200(4216)

292(286)

590(615)

688(703)

765(780)

[Cu(LH)]2 Cu2C30H18N4O10S2Cl2 90 8745b(8560)

1470(1484)

4186(4206)

200(210)

640(654)

728(748)

815(829)


1320(1324)

4126(4130)

340(344)

562(567)

642(648)

714(719)


1774(1748)

3675(3680)

284(288)

534(537)

609(613)

675(680)


1720(1724)

3662(3666)

300(306)

498(503)

570(575)

632(638)









2 [Cu(LH)]

2 [Zn(LH)(MeOH)

2]


2(LH)(MeOH)

2] The








2(IV)







RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH



4LH3 + [Zr4(OH)8(H2O)16](CH3COO)8

LH3 + [MoO2(acac)2]












](CndashO)(enolic)


Magmoment(BM)


[Co(LH)(MeOH)]2 1580 1365 1556 1385 mdash 1255 97592601322019280

486





2(IV) compound






2(IV)













6 The chem-




2]





1 119892(F) rarr 4T

2 119892(]1) 4T1 119892(F) rarr

4A2 119892(]2) and 4T

1 119892(F) rarr 4T










119892= 226 119892

perp= 207 119860

= 90 times 10


119892 and119892

perp








1205722


(1)


2is less





N

C

H

O

O

O

O

CC

H

O

C

C

Cl

SCo Co

N

N

S

Cl

C

C

O

H

CC

O

O

O

O

HC

N

H

H

A

A

[II A = MeOH]

S

H

Cu Cu

O

O

O

H

H Cl

C C

C

C

CS

N

NO

O

HC

C

OO

N

O

O

Cl

H

CN

H

C C

O

[III]

A

AN

O

C

O

O

C

S

O

ClC

HN

OH

C

CH Zn

[IV A = MeOH]

HO

A

N CC

H

NCH

Cl

C

OO

SOH

C

O

O

OZr

H

[V A = MeOH]

O

S

O

H

C

C

OH

O

N

Mo

O

OCl

CNC

C

O

A AH

[VI A = MeOH]

Figure 2






4 Conclusion





2(II)



[MoO2(LH)(MeOH)



2] (IV) as shown in

Figure 2

Disclosure





Acknowledgment


References











































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH

RefluxMeOH



4LH3 + [Zr4(OH)8(H2O)16](CH3COO)8

LH3 + [MoO2(acac)2]












](CndashO)(enolic)


Magmoment(BM)


[Co(LH)(MeOH)]2 1580 1365 1556 1385 mdash 1255 97592601322019280

486





2(IV) compound






2(IV)













6 The chem-




2]





1 119892(F) rarr 4T

2 119892(]1) 4T1 119892(F) rarr

4A2 119892(]2) and 4T

1 119892(F) rarr 4T










119892= 226 119892

perp= 207 119860

= 90 times 10


119892 and119892

perp








1205722


(1)


2is less





N

C

H

O

O

O

O

CC

H

O

C

C

Cl

SCo Co

N

N

S

Cl

C

C

O

H

CC

O

O

O

O

HC

N

H

H

A

A

[II A = MeOH]

S

H

Cu Cu

O

O

O

H

H Cl

C C

C

C

CS

N

NO

O

HC

C

OO

N

O

O

Cl

H

CN

H

C C

O

[III]

A

AN

O

C

O

O

C

S

O

ClC

HN

OH

C

CH Zn

[IV A = MeOH]

HO

A

N CC

H

NCH

Cl

C

OO

SOH

C

O

O

OZr

H

[V A = MeOH]

O

S

O

H

C

C

OH

O

N

Mo

O

OCl

CNC

C

O

A AH

[VI A = MeOH]

Figure 2






4 Conclusion





2(II)



[MoO2(LH)(MeOH)



2] (IV) as shown in

Figure 2

Disclosure





Acknowledgment


References











































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of



2]





1 119892(F) rarr 4T

2 119892(]1) 4T1 119892(F) rarr

4A2 119892(]2) and 4T

1 119892(F) rarr 4T










119892= 226 119892

perp= 207 119860

= 90 times 10


119892 and119892

perp








1205722


(1)


2is less





N

C

H

O

O

O

O

CC

H

O

C

C

Cl

SCo Co

N

N

S

Cl

C

C

O

H

CC

O

O

O

O

HC

N

H

H

A

A

[II A = MeOH]

S

H

Cu Cu

O

O

O

H

H Cl

C C

C

C

CS

N

NO

O

HC

C

OO

N

O

O

Cl

H

CN

H

C C

O

[III]

A

AN

O

C

O

O

C

S

O

ClC

HN

OH

C

CH Zn

[IV A = MeOH]

HO

A

N CC

H

NCH

Cl

C

OO

SOH

C

O

O

OZr

H

[V A = MeOH]

O

S

O

H

C

C

OH

O

N

Mo

O

OCl

CNC

C

O

A AH

[VI A = MeOH]

Figure 2






4 Conclusion





2(II)



[MoO2(LH)(MeOH)



2] (IV) as shown in

Figure 2

Disclosure





Acknowledgment


References











































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


N

C

H

O

O

O

O

CC

H

O

C

C

Cl

SCo Co

N

N

S

Cl

C

C

O

H

CC

O

O

O

O

HC

N

H

H

A

A

[II A = MeOH]

S

H

Cu Cu

O

O

O

H

H Cl

C C

C

C

CS

N

NO

O

HC

C

OO

N

O

O

Cl

H

CN

H

C C

O

[III]

A

AN

O

C

O

O

C

S

O

ClC

HN

OH

C

CH Zn

[IV A = MeOH]

HO

A

N CC

H

NCH

Cl

C

OO

SOH

C

O

O

OZr

H

[V A = MeOH]

O

S

O

H

C

C

OH

O

N

Mo

O

OCl

CNC

C

O

A AH

[VI A = MeOH]

Figure 2






4 Conclusion





2(II)



[MoO2(LH)(MeOH)



2] (IV) as shown in

Figure 2

Disclosure





Acknowledgment


References











































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


Acknowledgment


References











































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of














Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of

)joebxj1vcmjtijoh$psqpsbujpo +pvsobmpg$ifnjtusz...

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