Research Article Synthesis, Characterization, and...
6
Hindawi Publishing Corporation Journal of Chemistry Volume 2013, Article ID 479343, 5 pages http://dx.doi.org/10.1155/2013/479343 Research Article Synthesis, Characterization, and Antimicrobial Studies of N, O Donor Schiff Base Polymeric Complexes Shubhangi N. Kotkar 1 and Harjeet D. Juneja 2 1 Government Polytechnic, Gondia, Maharashtra 441601, India 2 Department of Chemistry, RTMNU, Nagpur, Maharashtra 440033, India Correspondence should be addressed to Shubhangi N. Kotkar; [email protected] Received 9 May 2013; Revised 1 August 2013; Accepted 1 August 2013 Academic Editor: Antonio Manuel Romerosa-Nievas Copyright © 2013 S. N. Kotkar and H. D. Juneja. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. A series of new polymeric complexes of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) were prepared with a Schiff base ligand derived from condensation of 2,4-dihydroxy acetophenone and p-phenylene diamine and characterized by elemental analysis and IR and NMR spectral data. e antimicrobial activity of the Schiff base and its polymeric complexes have been studied. 1. Introduction Compounds containing imines bases have found exten- sive applications in organic synthesis [1]; several of these molecules display significant biological activity. In the last decade Schiff base ligands [2–4] have received more attention mainly because of their wide applications in the field of catal- ysis [5] and due to their antimicrobial [6–8] and antifungal activity [9]. Schiff bases play an important role in inorganic chemistry as they can easily form stable complexes with most transition metal ions [10, 11]. e development of the field of bioinor- ganic chemistry has increased the interest in Schiff base complexes, since it has been recognized that many of these complexes may serve as models for biologically important species. Schiff base metal complexes were investigated for fungicidal, fungistatic, bactericidal, and bacteriostatic activi- ties [12–15]. e condensation reaction between 2,4-dihydroxy ace- tophenone and p-phenylene diamine yields a new compound with mainly two donor sites suitable for the study of ligational behavior which attracted our attention to synthesize Schiff’s base which has been used for the preparation of the metal complexes of transition metals such as Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) [16]. In the present work, the structures of synthesized bis-bidentate ligand and its polymeric metal complexes with Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) ions have been characterized by various physicochemical techniques, namely, elemental analysis and IR and NMR spectral studies, and were also screened for antibacterial activities against some species of pathogenic bacteria. 2. Experimental 2.1. Materials and Methodology. All the chemicals used were of analytical grade. Solvents used were of analytical grade and purified by standard procedures. 2.2. Synthesis of Ligand. Synthesis of ligand was carried out in two steps. e first step involved the preparation of 2,4- dihydroxy acetophenone while the second step involved the preparation of ligand. 2.2.1. Synthesis of 2,4-Dihydroxy Acetophenone. Anhydrous ZnCl 2 (70 g) was dissolved in glacial acetic acid (65 mL) in a 500 mL beaker. e solution was heated on wire gauge up to 140 ∘ C, and resorcinol (45 g) was added slowly with constant stirring. e temperature then raised up to 152 ∘ C, and the solution began to boil. It was allowed to stand for 30 min and diluted with HCl (50%). e resulting orange colored solid was collected, washed with dil. HCl (200 mL), and crystallized from water. e yield was found to be 80%, and
Transcript of Research Article Synthesis, Characterization, and...
![Page 1: Research Article Synthesis, Characterization, and ...downloads.hindawi.com/journals/jchem/2013/479343.pdfcm 1 consistent with the iminic absorption of free Schi base [ ]. e band for](https://reader034.fdocuments.net/reader034/viewer/2022050101/5f40419557383b1ae3684685/html5/thumbnails/1.jpg)
Hindawi Publishing CorporationJournal of ChemistryVolume 2013 Article ID 479343 5 pageshttpdxdoiorg1011552013479343
Research ArticleSynthesis Characterization and Antimicrobial Studies ofN O Donor Schiff Base Polymeric Complexes
Shubhangi N Kotkar1 and Harjeet D Juneja2
1 Government Polytechnic Gondia Maharashtra 441601 India2Department of Chemistry RTMNU Nagpur Maharashtra 440033 India
Correspondence should be addressed to Shubhangi N Kotkar snkotkar21gmailcom
Received 9 May 2013 Revised 1 August 2013 Accepted 1 August 2013
Academic Editor Antonio Manuel Romerosa-Nievas
Copyright copy 2013 S N Kotkar and H D JunejaThis is an open access article distributed under theCreative CommonsAttributionLicense which permits unrestricted use distribution and reproduction in anymedium provided the originalwork is properly cited
A series of new polymeric complexes of Mn(II) Co(II) Ni(II) Cu(II) and Zn(II) were prepared with a Schiff base ligand derivedfrom condensation of 24-dihydroxy acetophenone and p-phenylene diamine and characterized by elemental analysis and IR andNMR spectral data The antimicrobial activity of the Schiff base and its polymeric complexes have been studied
1 Introduction
Compounds containing imines bases have found exten-sive applications in organic synthesis [1] several of thesemolecules display significant biological activity In the lastdecade Schiff base ligands [2ndash4] have receivedmore attentionmainly because of their wide applications in the field of catal-ysis [5] and due to their antimicrobial [6ndash8] and antifungalactivity [9]
Schiff bases play an important role in inorganic chemistryas they can easily form stable complexes with most transitionmetal ions [10 11] The development of the field of bioinor-ganic chemistry has increased the interest in Schiff basecomplexes since it has been recognized that many of thesecomplexes may serve as models for biologically importantspecies Schiff base metal complexes were investigated forfungicidal fungistatic bactericidal and bacteriostatic activi-ties [12ndash15]
The condensation reaction between 24-dihydroxy ace-tophenone and p-phenylene diamine yields a new compoundwithmainly two donor sites suitable for the study of ligationalbehavior which attracted our attention to synthesize Schiff rsquosbase which has been used for the preparation of the metalcomplexes of transitionmetals such asMn(II) Co(II) Ni(II)Cu(II) and Zn(II) [16]
In the present work the structures of synthesizedbis-bidentate ligand and its polymeric metal complexes
with Mn(II) Co(II) Ni(II) Cu(II) and Zn(II) ions havebeen characterized by various physicochemical techniquesnamely elemental analysis and IR and NMR spectral studiesand were also screened for antibacterial activities againstsome species of pathogenic bacteria
2 Experimental
21 Materials and Methodology All the chemicals used wereof analytical grade Solvents used were of analytical grade andpurified by standard procedures
22 Synthesis of Ligand Synthesis of ligand was carried outin two steps The first step involved the preparation of 24-dihydroxy acetophenone while the second step involved thepreparation of ligand
221 Synthesis of 24-Dihydroxy Acetophenone AnhydrousZnCl2(70 g) was dissolved in glacial acetic acid (65mL) in a
500mL beaker The solution was heated on wire gauge up to140∘C and resorcinol (45 g) was added slowly with constantstirring The temperature then raised up to 152∘C and thesolution began to boil It was allowed to stand for 30minand diluted with HCl (50) The resulting orange coloredsolid was collected washed with dil HCl (200mL) andcrystallized from water The yield was found to be 80 and
2 Journal of Chemistry
Table 1 Analytical and physical data of the compound studied
Compound Colour Empirical formula Mol Wt C Cal (found) H Cal (found) N Cal (found)L Orange C22H20N2O4 37641 7013 (7015) 531 (535) 743 (739)[Mn(II)L] 2H2O Brown C22H18N2O4Mnsdot2H2O 46534 5673 (5680) 472 (480) 601 (614)[Co(II)L] 2H2O Bluish black C22H18N2O4Cosdot2H2O 46934 5624 (5633) 368 (392) 596 (598)[Ni(II)L] 2H2O Grey C22H18N2O4Nisdot2H2O 46910 5627 (5640) 468 (499) 596 (599)[Cu(II)L] Shining black C22H18N2O4Cu 43795 6028 (6035) 411 (420) 639 (646)[Zn(II)L] Whitish C22H18N2O4Zn 43981 6002 (6008) 409 (416) 636 (639)
HO OH HO OH
O
Resorcinol Resacetophenone
CH3COOHZnCl2
Scheme 1 Synthesis of resacetophenone
themelting point was found to be 144∘C Scheme 1 representsits synthesis
222 Synthesis of NN1015840-14-Phenylene Bis(24-DihydroxyAcetophenonylidene Imine) 24-dihydroxy acetophenone(005M 76 g) and p-phenylene diamine (0025M 27 g)were placed in round bottomed flask in distilled ethanolicmedium and few drops of acetic acid were added as acatalyst The reaction mixture was refluxed on sand bath for1 hr and then poured on crushed ice to get yellow-orangecrystals of Schiff base ligand NN1015840-14-phenylene bis(24-dihydroxy acetophenonylidene imine) The precipitatedcrystals of Schiff base were filtered and recrystallised withaqueous ethanol and dried The yield was found to be 65and the melting point was found to be 125∘C Scheme 2represents synthesis of ligand
223 Synthesis of Polymeric Complexes NN1015840-14-Phenylenebis(24-dihydroxy acetophenonylidene imine) (1mol) wasdissolved in distilled methanol and then added to the metalacetate (1mol) in distilled methanol The reaction mixturewas then refluxed on water bath for 2 hr and kept at roomtemperature for overnight The precipitated complex wasthen filtered under suction and washed successively with hotwater and methanol to remove unreacted ligand and metalacetate if any present and then dried
3 Results and Discussion
The stoichiometry of the ligand and its polymeric complexeswere confirmed by their elemental analysis The elementalanalysis of the ligand and its metal complexes show goodsupport with the proposed structures of the ligand and itscomplexes and have been reported in Table 1
31 Infrared Spectral Analysis of Schiff Base Ligand IR spectraof ligand L show an intense band at 3299 cmminus1 indicating thepresence of phenolic OH group This sharp band is absentin the spectra of complexes indicting that the phenolic OHgroup is deprotonated and involved in coordination withmetal [17]
The ligand shows an intense band due to ] (C=N) ofazomethine group at around 1608 cmminus1 consistent with theiminic absorption of free Schiff base [18] The band forphenolic CndashO stretching is seen at 1516 cmminus1 The mediumintense band at 3302ndash3362 cmminus1 which is the characteristicof strong hydrogen bonded OndashH vibration shows existenceof intramolecular H bonding between phenolic oxygen andazomethine nitrogen [19]
32 Infrared Spectral Analysis of Schiff Base Complexes Inall complexes the band for azomethine group undergoes ashift to lower energy indicating coordination of azomethinenitrogenwithmetal ion [20 21]This fact is further supportedby appearance of some new bands ] (MndashN) at 630ndash667 cmminus1and (MndashO) at 410ndash491 cmminus1 in the spectra of complexes [22]In the complex broad band from 3200 to 3600 cmminus1 may beassigned to presence of lattice water In addition to abovebands the IR bands due to phenyl ring systems between 1520and 1566 cmminus1 which are almost unaffected in the complexhave been assigned to aromatic ] (C=C) In all complexesthe band for phenolic (CndashO) stretching shows a marked shiftof 17ndash25 cmminus1 to higher wave number due to the CndashOndashMbond formation [23]The band for intramolecular H bondingis absent in complexes indicating deprotonation of phenolicndashOH group and coordination with metal [24] Bands at 745ndash780 cmminus1 may attribute to rocking and wagging modes of thecoordinated water This band is absent in the spectra of CuLand ZnL indicating absence of coordinated water
It is concluded from the significant shift of free ligand] (C=N) to lower wave number side increased wave numberfor phenolic ] (CndashO) stretching band in complexes thatbonding of the ligand tometal ion is through phenolic oxygenand azomethine nitrogen The data of IR is tabulated inTable 2
33 1H NMR Analysis of Ligand and Its Polymeric Complexes1H NMR spectra of ligand at 400MHz in DMSO exhibit asinglet at 120575 = 126 ppm for phenolic ndashOH and multiplets inthe aromatic region 120575 = 63 to 75 ppm corresponding to
Journal of Chemistry 3
HO HOOH OH
O O
HO OH
N
N
HO OH
24-Dihydroxy acetophenone P-phenylene diamine 24-Dihydroxy acetophenone
H2N NH2
+ +
NN998400-14-phenylene bis(24-dihydroxy acetophenonylidene imine)
Scheme 2
Table 2 Infrared absorption frequencies (cmminus1) of ligand and itspolymeric complexes
S number Compoundcode
](ArndashOH)
](C=N)
](MndashN)
](MndashO)
](CndashO)
1 L 33023362 1608 mdash mdash 1516
2 MnL mdash 1605 630 410 15603 CoL mdash 1590 565 412 15204 NiL mdash 1585 667 428 15665 CuL mdash 1604 650 422 15326 ZnL mdash 1603 667 491 1522
benzene rings The NMR signal at 120575 = 25 ppm as a sharpand singlet peak is due to ndashCH
3proton [25]
1H NMR spectra of complexes at 400MHz in DMSOshow no peak corresponding to the presence of phenolicndashOH thus indicating removal of hydrogen and coordina-tion of metal to ligand through phenolic oxygen Peakscorresponding to benzene rings are also present in spectraof complexes without any change Retention of peaks inaromatic region without any formal change indicates thepreservation of the formal structure of ligand without anydeformation The structure of polymeric compounds hasbeen shown in Figure 1
34 Antimicrobial Activity of Ligand and Its Polymeric Com-plexes Synthesized Schiff bases and their correspondingmixed ligand metal complexes were screened against E coliS aureus B subtilis and P aeruginosa to assess their potentialas antimicrobial agent by well-diffusionmethod also called asagar ditch method The zones of inhibition based upon zonesize weremeasuredThemeasured zones of inhibition againstthe growth of various microorganisms have been listed inTable 3
From Table 3 it has been found that all complexes showgreater antibacterial activity than that of ligand [26] CuL
Table 3 Minimum inhibitory zones for ligand and complexes
Sample Conc (120583g) Zone of inhibition in mm againstS aureus E coli B subtilis P aeruginosa
L
025 12 11 10 1105 14 12 12 13075 15 13 15 1510 16 15 20 18
MnL
025 19 19 22 1805 23 21 25 22075 25 24 27 2610 28 25 30 31
CoL
025 14 mdash 12 1305 17 mdash 14 21075 19 15 17 2510 22 20 19 27
NiL
025 12 19 12 1605 15 21 16 21075 18 23 21 2310 20 24 24 26
CuL
025 14 20 14 1805 16 23 17 20075 19 25 19 2210 22 27 24 24
ZnL
025 13 11 23 1105 16 12 27 22075 mdash 14 31 3310 25 17 36 33
and MnL show very good results against all bacterial strainsFurthermore ZnL shows very good antibacterial activityagainst B subtilis
4 Journal of Chemistry
M = Mn2+ Co2+ Ni2+ Cu2+ Zn2+
n
N
N
O
HO
OH
O
M
M
Figure 1 Structure of the polymeric compounds
4 Conclusion
From the characterization of ligand and complexes usingCHN analysis IR and NMR structures of ligand and com-plexes were proposed Measurements of inhibition zones ofligand and complexes at different concentrations show thatall complexes have enhanced bactericidal activity more thanligand
References
[1] A S Shakeel N V Kalyane S R Karjgi and M L AhmedldquoSynthesis and antibacterial activity of new Schiff rsquos basesrdquoInternational Journal of Pharmacy and Life Sciences no 5 pp246ndash249 2010
[2] R Johari G Kumar and S Singh ldquoSynthesis and antibacterialactivity of M (II) Schiff base complexrdquo Journal of the IndianCouncil of Chemists vol 26 pp 23ndash27 2009
[3] J H Pandya and M K Shah ldquoSynthesis and antimicrobialproperties of transition metal complexes of novel Schiff baseligand derived from 5-bromosalicyldehyderdquo Journal of theIndian Council of Chemists vol 26 no 2 pp 109ndash112 2009
[4] S Varghese and M K Muraleedharan Nair ldquoSpectroscopicand antimicrobial studies of some 2-hydroxybenzilidene-3-aminophenol complexesrdquo Research Journal of PharmaceuticalBiological and Chemical Sciences vol 1 no 2 pp 347ndash353 2010
[5] S Kumar D N Dhar and P N Saxena ldquoApplications of metalcomplexes of Schiff bases-a reviewrdquo Journal of Scientific andIndustrial Research vol 68 no 3 pp 181ndash187 2009
[6] F M Morad M M E L Ajaily and S Ben-Gweirif ldquoPrepara-tion physical characterization and antibacterial activity of Ni(II) Schiff base complexrdquo Journal of Science and Its Applicationsvol 1 pp 72ndash78 2007
[7] P Singh and R K S Dhakarey ldquoSynthesis characterizationand antimicrobial studies of metal complexes with Schiff basesderived from 2-thienyl glyoxalrdquo Rasayan Journal of Chemistryvol 2 no 4 pp 869ndash874 2009
[8] J Salimon N Salih E Yousif A Hameed and H IbraheemldquoSynthesis characterization and biological activity of Schiffbases of 2 5-dimercapto-134-thiadiazolerdquo Australian Journalof Basic and Applied Sciences vol 4 no 7 pp 2016ndash2021 2010
[9] K S S Lamani O KotreshM A Phaniband and J C KadakolldquoSynthesis characterization and antimicrobial properties ofSchiff bases derived from condensation of 8-formyl-7-hydroxy-4-methylcoumarin and substituted triazole derivativesrdquo E-Journal of Chemistry vol 6 supplement 1 pp S239ndashS246 2009
[10] A M Hamil K M Khalifa A Al-Houni and M M El-AjailyldquoSynthesis spectroscopic investigation and antiactivity activityof Schiff base complexes of cobalt (II) and copper (II) ionsrdquoRasayan Journal of Chemistry vol 2 no 2 pp 261ndash266 2009
[11] A P Mishra and N Sharma ldquoSynthesis characterization X-ray and thermal studies of some Schiff base metal complexesrdquoJournal of the Indian Council of Chemists vol 26 pp 125ndash1292009
[12] T Rosu S Pasculescu V Lazar C Chifiriuc and R CernatldquoCopper(II) complexes with ligands derived from 4-amino-23-dimethyl-1-phenyl-3-pyrazolin-5-one synthesis and biologicalactivityrdquoMolecules vol 11 no 11 pp 904ndash914 2006
[13] N S Gwaram H M Ali M A Abdulla et al ldquoAntibacterialevaluation of some Schiff bases derived from 2-acetylpyridineand their metal complexesrdquo Molecules vol 17 no 5 pp 5952ndash5971 2012
[14] K T Joshi AM Pancholi K S Pandya and A SThakar ldquoSyn-thesis characterization and antibacterial activity of novel Schiffbase derived from 4-acetyl-3-methyl-1-(4rsquo-Methyl-Phenyl)-2-Pyrazolin-5-one and its transition metal complexesrdquo Interna-tional Journal of Research in Chemistry and Environment vol1 no 2 pp 263ndash269 2011
[15] A P Mishra R Mishra R Jain and S Gupta ldquoSynthesisof new VO(II) Co(II) Ni(II) and Cu(II) complexes withisatin-3- chloro-4-floroaniline and 2-pyridinecarboxylidene-4aminoantipyrine and their antimicrobial studiesrdquo The KoreanSociety of Mycology vol 40 no 1 pp 20ndash26 2012
[16] A Prakash M P Gangwar and K K Singh ldquoSynthesis spec-troscopy and biological studies of nickel (II) complexes withtetradentate Schiff bases having N
2O2donor grouprdquo Journal of
Developmental Biology and Tissue Engineering vol 3 no 2 pp13ndash19 2011
[17] A S Munde A N Jagdale S M Jadhav and T K ChondhekarldquoSynthesis characterization and thermal study of some tran-sition metal complexes of an asymmetrical tetradentate Schiffbase ligandrdquo Journal of the Serbian Chemical Society vol 75 no3 pp 349ndash359 2010
[18] U K Singh S N Pandeya S K Sethia et al ldquoSynthesisand biological evaluation of some sulfonamide Schiff rsquos basesrdquoInternational Journal of Pharmaceutical Sciences and DrugResearch vol 2 no 3 pp 216ndash218 2010
[19] N Raman J DhaveethuRaja andA Sakthivel ldquoSynthesis spec-tral characterization of Schiff base transition metal complexesDNA cleavage and antimicrobial activity studiesrdquo Journal ofChemical Sciences vol 119 no 4 pp 303ndash310 2007
[20] V ReddyN Patil and S D Angadi ldquoSynthesis characterizationand antimicrobial activity of Cu(II) Co(II) and Ni(II) com-plexes with O N and S donor ligandsrdquo E-Journal of Chemistryvol 5 no 3 pp 577ndash583 2008
Journal of Chemistry 5
[21] K Nakamato Infrared Spectra of Inorganic and CoordinationCompounds John Wiley New York NY USA 1970
[22] S Joshi V Pawar and V Uma ldquoSynthesis characterization andbiological studies of Schiff bases metal complexes Co (II) Zn(II) Ni (II) and Mn (II) derived from amoxicillin trihydratewith various aldehydesrdquo International Journal of Pharma andBio Sciences vol 2 no 1 pp 240ndash250 2011
[23] J T Makode and A S Aswar ldquoSynthesis characterizationbiological and thermal properties of some new Schiff basecomplexes derived from 2-hydroxy-5-chloroacetophenone andS-methyldithiocarbazaterdquo Indian Journal of Chemistry A vol43 no 10 pp 2120ndash2125 2004
[24] A K Mapari and K V Mangaonkar ldquoSynthesis characteri-zation and antimicrobial activity of mixed Schiff base ligandcomplexes of transition metal (II) ionsrdquo International Journalof ChemTech Research vol 3 no 1 pp 477ndash482 2011
[25] P Venkatesh ldquoSynthesis charecterisation and anti microbialactivity of various Schiff base complex of zinc(II) and copper(II) ionsrdquo Asian Journal of Pharmaceutical and Health Sciencesvol 1 pp 8ndash11 2011
[26] M Revanasiddappa T Suresh S Khasim S C RaghavendrayC Basavaraja and S D Angadi ldquoTransition metal complexesof 1 4(21015840-hydroxyphenyl-1-yl) di-imino azine synthesis char-acterization and antimicrobial studiesrdquo E-Journal of Chemistryvol 5 no 2 pp 395ndash403 2008
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CatalystsJournal of
![Page 2: Research Article Synthesis, Characterization, and ...downloads.hindawi.com/journals/jchem/2013/479343.pdfcm 1 consistent with the iminic absorption of free Schi base [ ]. e band for](https://reader034.fdocuments.net/reader034/viewer/2022050101/5f40419557383b1ae3684685/html5/thumbnails/2.jpg)
2 Journal of Chemistry
Table 1 Analytical and physical data of the compound studied
Compound Colour Empirical formula Mol Wt C Cal (found) H Cal (found) N Cal (found)L Orange C22H20N2O4 37641 7013 (7015) 531 (535) 743 (739)[Mn(II)L] 2H2O Brown C22H18N2O4Mnsdot2H2O 46534 5673 (5680) 472 (480) 601 (614)[Co(II)L] 2H2O Bluish black C22H18N2O4Cosdot2H2O 46934 5624 (5633) 368 (392) 596 (598)[Ni(II)L] 2H2O Grey C22H18N2O4Nisdot2H2O 46910 5627 (5640) 468 (499) 596 (599)[Cu(II)L] Shining black C22H18N2O4Cu 43795 6028 (6035) 411 (420) 639 (646)[Zn(II)L] Whitish C22H18N2O4Zn 43981 6002 (6008) 409 (416) 636 (639)
HO OH HO OH
O
Resorcinol Resacetophenone
CH3COOHZnCl2
Scheme 1 Synthesis of resacetophenone
themelting point was found to be 144∘C Scheme 1 representsits synthesis
222 Synthesis of NN1015840-14-Phenylene Bis(24-DihydroxyAcetophenonylidene Imine) 24-dihydroxy acetophenone(005M 76 g) and p-phenylene diamine (0025M 27 g)were placed in round bottomed flask in distilled ethanolicmedium and few drops of acetic acid were added as acatalyst The reaction mixture was refluxed on sand bath for1 hr and then poured on crushed ice to get yellow-orangecrystals of Schiff base ligand NN1015840-14-phenylene bis(24-dihydroxy acetophenonylidene imine) The precipitatedcrystals of Schiff base were filtered and recrystallised withaqueous ethanol and dried The yield was found to be 65and the melting point was found to be 125∘C Scheme 2represents synthesis of ligand
223 Synthesis of Polymeric Complexes NN1015840-14-Phenylenebis(24-dihydroxy acetophenonylidene imine) (1mol) wasdissolved in distilled methanol and then added to the metalacetate (1mol) in distilled methanol The reaction mixturewas then refluxed on water bath for 2 hr and kept at roomtemperature for overnight The precipitated complex wasthen filtered under suction and washed successively with hotwater and methanol to remove unreacted ligand and metalacetate if any present and then dried
3 Results and Discussion
The stoichiometry of the ligand and its polymeric complexeswere confirmed by their elemental analysis The elementalanalysis of the ligand and its metal complexes show goodsupport with the proposed structures of the ligand and itscomplexes and have been reported in Table 1
31 Infrared Spectral Analysis of Schiff Base Ligand IR spectraof ligand L show an intense band at 3299 cmminus1 indicating thepresence of phenolic OH group This sharp band is absentin the spectra of complexes indicting that the phenolic OHgroup is deprotonated and involved in coordination withmetal [17]
The ligand shows an intense band due to ] (C=N) ofazomethine group at around 1608 cmminus1 consistent with theiminic absorption of free Schiff base [18] The band forphenolic CndashO stretching is seen at 1516 cmminus1 The mediumintense band at 3302ndash3362 cmminus1 which is the characteristicof strong hydrogen bonded OndashH vibration shows existenceof intramolecular H bonding between phenolic oxygen andazomethine nitrogen [19]
32 Infrared Spectral Analysis of Schiff Base Complexes Inall complexes the band for azomethine group undergoes ashift to lower energy indicating coordination of azomethinenitrogenwithmetal ion [20 21]This fact is further supportedby appearance of some new bands ] (MndashN) at 630ndash667 cmminus1and (MndashO) at 410ndash491 cmminus1 in the spectra of complexes [22]In the complex broad band from 3200 to 3600 cmminus1 may beassigned to presence of lattice water In addition to abovebands the IR bands due to phenyl ring systems between 1520and 1566 cmminus1 which are almost unaffected in the complexhave been assigned to aromatic ] (C=C) In all complexesthe band for phenolic (CndashO) stretching shows a marked shiftof 17ndash25 cmminus1 to higher wave number due to the CndashOndashMbond formation [23]The band for intramolecular H bondingis absent in complexes indicating deprotonation of phenolicndashOH group and coordination with metal [24] Bands at 745ndash780 cmminus1 may attribute to rocking and wagging modes of thecoordinated water This band is absent in the spectra of CuLand ZnL indicating absence of coordinated water
It is concluded from the significant shift of free ligand] (C=N) to lower wave number side increased wave numberfor phenolic ] (CndashO) stretching band in complexes thatbonding of the ligand tometal ion is through phenolic oxygenand azomethine nitrogen The data of IR is tabulated inTable 2
33 1H NMR Analysis of Ligand and Its Polymeric Complexes1H NMR spectra of ligand at 400MHz in DMSO exhibit asinglet at 120575 = 126 ppm for phenolic ndashOH and multiplets inthe aromatic region 120575 = 63 to 75 ppm corresponding to
Journal of Chemistry 3
HO HOOH OH
O O
HO OH
N
N
HO OH
24-Dihydroxy acetophenone P-phenylene diamine 24-Dihydroxy acetophenone
H2N NH2
+ +
NN998400-14-phenylene bis(24-dihydroxy acetophenonylidene imine)
Scheme 2
Table 2 Infrared absorption frequencies (cmminus1) of ligand and itspolymeric complexes
S number Compoundcode
](ArndashOH)
](C=N)
](MndashN)
](MndashO)
](CndashO)
1 L 33023362 1608 mdash mdash 1516
2 MnL mdash 1605 630 410 15603 CoL mdash 1590 565 412 15204 NiL mdash 1585 667 428 15665 CuL mdash 1604 650 422 15326 ZnL mdash 1603 667 491 1522
benzene rings The NMR signal at 120575 = 25 ppm as a sharpand singlet peak is due to ndashCH
3proton [25]
1H NMR spectra of complexes at 400MHz in DMSOshow no peak corresponding to the presence of phenolicndashOH thus indicating removal of hydrogen and coordina-tion of metal to ligand through phenolic oxygen Peakscorresponding to benzene rings are also present in spectraof complexes without any change Retention of peaks inaromatic region without any formal change indicates thepreservation of the formal structure of ligand without anydeformation The structure of polymeric compounds hasbeen shown in Figure 1
34 Antimicrobial Activity of Ligand and Its Polymeric Com-plexes Synthesized Schiff bases and their correspondingmixed ligand metal complexes were screened against E coliS aureus B subtilis and P aeruginosa to assess their potentialas antimicrobial agent by well-diffusionmethod also called asagar ditch method The zones of inhibition based upon zonesize weremeasuredThemeasured zones of inhibition againstthe growth of various microorganisms have been listed inTable 3
From Table 3 it has been found that all complexes showgreater antibacterial activity than that of ligand [26] CuL
Table 3 Minimum inhibitory zones for ligand and complexes
Sample Conc (120583g) Zone of inhibition in mm againstS aureus E coli B subtilis P aeruginosa
L
025 12 11 10 1105 14 12 12 13075 15 13 15 1510 16 15 20 18
MnL
025 19 19 22 1805 23 21 25 22075 25 24 27 2610 28 25 30 31
CoL
025 14 mdash 12 1305 17 mdash 14 21075 19 15 17 2510 22 20 19 27
NiL
025 12 19 12 1605 15 21 16 21075 18 23 21 2310 20 24 24 26
CuL
025 14 20 14 1805 16 23 17 20075 19 25 19 2210 22 27 24 24
ZnL
025 13 11 23 1105 16 12 27 22075 mdash 14 31 3310 25 17 36 33
and MnL show very good results against all bacterial strainsFurthermore ZnL shows very good antibacterial activityagainst B subtilis
4 Journal of Chemistry
M = Mn2+ Co2+ Ni2+ Cu2+ Zn2+
n
N
N
O
HO
OH
O
M
M
Figure 1 Structure of the polymeric compounds
4 Conclusion
From the characterization of ligand and complexes usingCHN analysis IR and NMR structures of ligand and com-plexes were proposed Measurements of inhibition zones ofligand and complexes at different concentrations show thatall complexes have enhanced bactericidal activity more thanligand
References
[1] A S Shakeel N V Kalyane S R Karjgi and M L AhmedldquoSynthesis and antibacterial activity of new Schiff rsquos basesrdquoInternational Journal of Pharmacy and Life Sciences no 5 pp246ndash249 2010
[2] R Johari G Kumar and S Singh ldquoSynthesis and antibacterialactivity of M (II) Schiff base complexrdquo Journal of the IndianCouncil of Chemists vol 26 pp 23ndash27 2009
[3] J H Pandya and M K Shah ldquoSynthesis and antimicrobialproperties of transition metal complexes of novel Schiff baseligand derived from 5-bromosalicyldehyderdquo Journal of theIndian Council of Chemists vol 26 no 2 pp 109ndash112 2009
[4] S Varghese and M K Muraleedharan Nair ldquoSpectroscopicand antimicrobial studies of some 2-hydroxybenzilidene-3-aminophenol complexesrdquo Research Journal of PharmaceuticalBiological and Chemical Sciences vol 1 no 2 pp 347ndash353 2010
[5] S Kumar D N Dhar and P N Saxena ldquoApplications of metalcomplexes of Schiff bases-a reviewrdquo Journal of Scientific andIndustrial Research vol 68 no 3 pp 181ndash187 2009
[6] F M Morad M M E L Ajaily and S Ben-Gweirif ldquoPrepara-tion physical characterization and antibacterial activity of Ni(II) Schiff base complexrdquo Journal of Science and Its Applicationsvol 1 pp 72ndash78 2007
[7] P Singh and R K S Dhakarey ldquoSynthesis characterizationand antimicrobial studies of metal complexes with Schiff basesderived from 2-thienyl glyoxalrdquo Rasayan Journal of Chemistryvol 2 no 4 pp 869ndash874 2009
[8] J Salimon N Salih E Yousif A Hameed and H IbraheemldquoSynthesis characterization and biological activity of Schiffbases of 2 5-dimercapto-134-thiadiazolerdquo Australian Journalof Basic and Applied Sciences vol 4 no 7 pp 2016ndash2021 2010
[9] K S S Lamani O KotreshM A Phaniband and J C KadakolldquoSynthesis characterization and antimicrobial properties ofSchiff bases derived from condensation of 8-formyl-7-hydroxy-4-methylcoumarin and substituted triazole derivativesrdquo E-Journal of Chemistry vol 6 supplement 1 pp S239ndashS246 2009
[10] A M Hamil K M Khalifa A Al-Houni and M M El-AjailyldquoSynthesis spectroscopic investigation and antiactivity activityof Schiff base complexes of cobalt (II) and copper (II) ionsrdquoRasayan Journal of Chemistry vol 2 no 2 pp 261ndash266 2009
[11] A P Mishra and N Sharma ldquoSynthesis characterization X-ray and thermal studies of some Schiff base metal complexesrdquoJournal of the Indian Council of Chemists vol 26 pp 125ndash1292009
[12] T Rosu S Pasculescu V Lazar C Chifiriuc and R CernatldquoCopper(II) complexes with ligands derived from 4-amino-23-dimethyl-1-phenyl-3-pyrazolin-5-one synthesis and biologicalactivityrdquoMolecules vol 11 no 11 pp 904ndash914 2006
[13] N S Gwaram H M Ali M A Abdulla et al ldquoAntibacterialevaluation of some Schiff bases derived from 2-acetylpyridineand their metal complexesrdquo Molecules vol 17 no 5 pp 5952ndash5971 2012
[14] K T Joshi AM Pancholi K S Pandya and A SThakar ldquoSyn-thesis characterization and antibacterial activity of novel Schiffbase derived from 4-acetyl-3-methyl-1-(4rsquo-Methyl-Phenyl)-2-Pyrazolin-5-one and its transition metal complexesrdquo Interna-tional Journal of Research in Chemistry and Environment vol1 no 2 pp 263ndash269 2011
[15] A P Mishra R Mishra R Jain and S Gupta ldquoSynthesisof new VO(II) Co(II) Ni(II) and Cu(II) complexes withisatin-3- chloro-4-floroaniline and 2-pyridinecarboxylidene-4aminoantipyrine and their antimicrobial studiesrdquo The KoreanSociety of Mycology vol 40 no 1 pp 20ndash26 2012
[16] A Prakash M P Gangwar and K K Singh ldquoSynthesis spec-troscopy and biological studies of nickel (II) complexes withtetradentate Schiff bases having N
2O2donor grouprdquo Journal of
Developmental Biology and Tissue Engineering vol 3 no 2 pp13ndash19 2011
[17] A S Munde A N Jagdale S M Jadhav and T K ChondhekarldquoSynthesis characterization and thermal study of some tran-sition metal complexes of an asymmetrical tetradentate Schiffbase ligandrdquo Journal of the Serbian Chemical Society vol 75 no3 pp 349ndash359 2010
[18] U K Singh S N Pandeya S K Sethia et al ldquoSynthesisand biological evaluation of some sulfonamide Schiff rsquos basesrdquoInternational Journal of Pharmaceutical Sciences and DrugResearch vol 2 no 3 pp 216ndash218 2010
[19] N Raman J DhaveethuRaja andA Sakthivel ldquoSynthesis spec-tral characterization of Schiff base transition metal complexesDNA cleavage and antimicrobial activity studiesrdquo Journal ofChemical Sciences vol 119 no 4 pp 303ndash310 2007
[20] V ReddyN Patil and S D Angadi ldquoSynthesis characterizationand antimicrobial activity of Cu(II) Co(II) and Ni(II) com-plexes with O N and S donor ligandsrdquo E-Journal of Chemistryvol 5 no 3 pp 577ndash583 2008
Journal of Chemistry 5
[21] K Nakamato Infrared Spectra of Inorganic and CoordinationCompounds John Wiley New York NY USA 1970
[22] S Joshi V Pawar and V Uma ldquoSynthesis characterization andbiological studies of Schiff bases metal complexes Co (II) Zn(II) Ni (II) and Mn (II) derived from amoxicillin trihydratewith various aldehydesrdquo International Journal of Pharma andBio Sciences vol 2 no 1 pp 240ndash250 2011
[23] J T Makode and A S Aswar ldquoSynthesis characterizationbiological and thermal properties of some new Schiff basecomplexes derived from 2-hydroxy-5-chloroacetophenone andS-methyldithiocarbazaterdquo Indian Journal of Chemistry A vol43 no 10 pp 2120ndash2125 2004
[24] A K Mapari and K V Mangaonkar ldquoSynthesis characteri-zation and antimicrobial activity of mixed Schiff base ligandcomplexes of transition metal (II) ionsrdquo International Journalof ChemTech Research vol 3 no 1 pp 477ndash482 2011
[25] P Venkatesh ldquoSynthesis charecterisation and anti microbialactivity of various Schiff base complex of zinc(II) and copper(II) ionsrdquo Asian Journal of Pharmaceutical and Health Sciencesvol 1 pp 8ndash11 2011
[26] M Revanasiddappa T Suresh S Khasim S C RaghavendrayC Basavaraja and S D Angadi ldquoTransition metal complexesof 1 4(21015840-hydroxyphenyl-1-yl) di-imino azine synthesis char-acterization and antimicrobial studiesrdquo E-Journal of Chemistryvol 5 no 2 pp 395ndash403 2008
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
![Page 3: Research Article Synthesis, Characterization, and ...downloads.hindawi.com/journals/jchem/2013/479343.pdfcm 1 consistent with the iminic absorption of free Schi base [ ]. e band for](https://reader034.fdocuments.net/reader034/viewer/2022050101/5f40419557383b1ae3684685/html5/thumbnails/3.jpg)
Journal of Chemistry 3
HO HOOH OH
O O
HO OH
N
N
HO OH
24-Dihydroxy acetophenone P-phenylene diamine 24-Dihydroxy acetophenone
H2N NH2
+ +
NN998400-14-phenylene bis(24-dihydroxy acetophenonylidene imine)
Scheme 2
Table 2 Infrared absorption frequencies (cmminus1) of ligand and itspolymeric complexes
S number Compoundcode
](ArndashOH)
](C=N)
](MndashN)
](MndashO)
](CndashO)
1 L 33023362 1608 mdash mdash 1516
2 MnL mdash 1605 630 410 15603 CoL mdash 1590 565 412 15204 NiL mdash 1585 667 428 15665 CuL mdash 1604 650 422 15326 ZnL mdash 1603 667 491 1522
benzene rings The NMR signal at 120575 = 25 ppm as a sharpand singlet peak is due to ndashCH
3proton [25]
1H NMR spectra of complexes at 400MHz in DMSOshow no peak corresponding to the presence of phenolicndashOH thus indicating removal of hydrogen and coordina-tion of metal to ligand through phenolic oxygen Peakscorresponding to benzene rings are also present in spectraof complexes without any change Retention of peaks inaromatic region without any formal change indicates thepreservation of the formal structure of ligand without anydeformation The structure of polymeric compounds hasbeen shown in Figure 1
34 Antimicrobial Activity of Ligand and Its Polymeric Com-plexes Synthesized Schiff bases and their correspondingmixed ligand metal complexes were screened against E coliS aureus B subtilis and P aeruginosa to assess their potentialas antimicrobial agent by well-diffusionmethod also called asagar ditch method The zones of inhibition based upon zonesize weremeasuredThemeasured zones of inhibition againstthe growth of various microorganisms have been listed inTable 3
From Table 3 it has been found that all complexes showgreater antibacterial activity than that of ligand [26] CuL
Table 3 Minimum inhibitory zones for ligand and complexes
Sample Conc (120583g) Zone of inhibition in mm againstS aureus E coli B subtilis P aeruginosa
L
025 12 11 10 1105 14 12 12 13075 15 13 15 1510 16 15 20 18
MnL
025 19 19 22 1805 23 21 25 22075 25 24 27 2610 28 25 30 31
CoL
025 14 mdash 12 1305 17 mdash 14 21075 19 15 17 2510 22 20 19 27
NiL
025 12 19 12 1605 15 21 16 21075 18 23 21 2310 20 24 24 26
CuL
025 14 20 14 1805 16 23 17 20075 19 25 19 2210 22 27 24 24
ZnL
025 13 11 23 1105 16 12 27 22075 mdash 14 31 3310 25 17 36 33
and MnL show very good results against all bacterial strainsFurthermore ZnL shows very good antibacterial activityagainst B subtilis
4 Journal of Chemistry
M = Mn2+ Co2+ Ni2+ Cu2+ Zn2+
n
N
N
O
HO
OH
O
M
M
Figure 1 Structure of the polymeric compounds
4 Conclusion
From the characterization of ligand and complexes usingCHN analysis IR and NMR structures of ligand and com-plexes were proposed Measurements of inhibition zones ofligand and complexes at different concentrations show thatall complexes have enhanced bactericidal activity more thanligand
References
[1] A S Shakeel N V Kalyane S R Karjgi and M L AhmedldquoSynthesis and antibacterial activity of new Schiff rsquos basesrdquoInternational Journal of Pharmacy and Life Sciences no 5 pp246ndash249 2010
[2] R Johari G Kumar and S Singh ldquoSynthesis and antibacterialactivity of M (II) Schiff base complexrdquo Journal of the IndianCouncil of Chemists vol 26 pp 23ndash27 2009
[3] J H Pandya and M K Shah ldquoSynthesis and antimicrobialproperties of transition metal complexes of novel Schiff baseligand derived from 5-bromosalicyldehyderdquo Journal of theIndian Council of Chemists vol 26 no 2 pp 109ndash112 2009
[4] S Varghese and M K Muraleedharan Nair ldquoSpectroscopicand antimicrobial studies of some 2-hydroxybenzilidene-3-aminophenol complexesrdquo Research Journal of PharmaceuticalBiological and Chemical Sciences vol 1 no 2 pp 347ndash353 2010
[5] S Kumar D N Dhar and P N Saxena ldquoApplications of metalcomplexes of Schiff bases-a reviewrdquo Journal of Scientific andIndustrial Research vol 68 no 3 pp 181ndash187 2009
[6] F M Morad M M E L Ajaily and S Ben-Gweirif ldquoPrepara-tion physical characterization and antibacterial activity of Ni(II) Schiff base complexrdquo Journal of Science and Its Applicationsvol 1 pp 72ndash78 2007
[7] P Singh and R K S Dhakarey ldquoSynthesis characterizationand antimicrobial studies of metal complexes with Schiff basesderived from 2-thienyl glyoxalrdquo Rasayan Journal of Chemistryvol 2 no 4 pp 869ndash874 2009
[8] J Salimon N Salih E Yousif A Hameed and H IbraheemldquoSynthesis characterization and biological activity of Schiffbases of 2 5-dimercapto-134-thiadiazolerdquo Australian Journalof Basic and Applied Sciences vol 4 no 7 pp 2016ndash2021 2010
[9] K S S Lamani O KotreshM A Phaniband and J C KadakolldquoSynthesis characterization and antimicrobial properties ofSchiff bases derived from condensation of 8-formyl-7-hydroxy-4-methylcoumarin and substituted triazole derivativesrdquo E-Journal of Chemistry vol 6 supplement 1 pp S239ndashS246 2009
[10] A M Hamil K M Khalifa A Al-Houni and M M El-AjailyldquoSynthesis spectroscopic investigation and antiactivity activityof Schiff base complexes of cobalt (II) and copper (II) ionsrdquoRasayan Journal of Chemistry vol 2 no 2 pp 261ndash266 2009
[11] A P Mishra and N Sharma ldquoSynthesis characterization X-ray and thermal studies of some Schiff base metal complexesrdquoJournal of the Indian Council of Chemists vol 26 pp 125ndash1292009
[12] T Rosu S Pasculescu V Lazar C Chifiriuc and R CernatldquoCopper(II) complexes with ligands derived from 4-amino-23-dimethyl-1-phenyl-3-pyrazolin-5-one synthesis and biologicalactivityrdquoMolecules vol 11 no 11 pp 904ndash914 2006
[13] N S Gwaram H M Ali M A Abdulla et al ldquoAntibacterialevaluation of some Schiff bases derived from 2-acetylpyridineand their metal complexesrdquo Molecules vol 17 no 5 pp 5952ndash5971 2012
[14] K T Joshi AM Pancholi K S Pandya and A SThakar ldquoSyn-thesis characterization and antibacterial activity of novel Schiffbase derived from 4-acetyl-3-methyl-1-(4rsquo-Methyl-Phenyl)-2-Pyrazolin-5-one and its transition metal complexesrdquo Interna-tional Journal of Research in Chemistry and Environment vol1 no 2 pp 263ndash269 2011
[15] A P Mishra R Mishra R Jain and S Gupta ldquoSynthesisof new VO(II) Co(II) Ni(II) and Cu(II) complexes withisatin-3- chloro-4-floroaniline and 2-pyridinecarboxylidene-4aminoantipyrine and their antimicrobial studiesrdquo The KoreanSociety of Mycology vol 40 no 1 pp 20ndash26 2012
[16] A Prakash M P Gangwar and K K Singh ldquoSynthesis spec-troscopy and biological studies of nickel (II) complexes withtetradentate Schiff bases having N
2O2donor grouprdquo Journal of
Developmental Biology and Tissue Engineering vol 3 no 2 pp13ndash19 2011
[17] A S Munde A N Jagdale S M Jadhav and T K ChondhekarldquoSynthesis characterization and thermal study of some tran-sition metal complexes of an asymmetrical tetradentate Schiffbase ligandrdquo Journal of the Serbian Chemical Society vol 75 no3 pp 349ndash359 2010
[18] U K Singh S N Pandeya S K Sethia et al ldquoSynthesisand biological evaluation of some sulfonamide Schiff rsquos basesrdquoInternational Journal of Pharmaceutical Sciences and DrugResearch vol 2 no 3 pp 216ndash218 2010
[19] N Raman J DhaveethuRaja andA Sakthivel ldquoSynthesis spec-tral characterization of Schiff base transition metal complexesDNA cleavage and antimicrobial activity studiesrdquo Journal ofChemical Sciences vol 119 no 4 pp 303ndash310 2007
[20] V ReddyN Patil and S D Angadi ldquoSynthesis characterizationand antimicrobial activity of Cu(II) Co(II) and Ni(II) com-plexes with O N and S donor ligandsrdquo E-Journal of Chemistryvol 5 no 3 pp 577ndash583 2008
Journal of Chemistry 5
[21] K Nakamato Infrared Spectra of Inorganic and CoordinationCompounds John Wiley New York NY USA 1970
[22] S Joshi V Pawar and V Uma ldquoSynthesis characterization andbiological studies of Schiff bases metal complexes Co (II) Zn(II) Ni (II) and Mn (II) derived from amoxicillin trihydratewith various aldehydesrdquo International Journal of Pharma andBio Sciences vol 2 no 1 pp 240ndash250 2011
[23] J T Makode and A S Aswar ldquoSynthesis characterizationbiological and thermal properties of some new Schiff basecomplexes derived from 2-hydroxy-5-chloroacetophenone andS-methyldithiocarbazaterdquo Indian Journal of Chemistry A vol43 no 10 pp 2120ndash2125 2004
[24] A K Mapari and K V Mangaonkar ldquoSynthesis characteri-zation and antimicrobial activity of mixed Schiff base ligandcomplexes of transition metal (II) ionsrdquo International Journalof ChemTech Research vol 3 no 1 pp 477ndash482 2011
[25] P Venkatesh ldquoSynthesis charecterisation and anti microbialactivity of various Schiff base complex of zinc(II) and copper(II) ionsrdquo Asian Journal of Pharmaceutical and Health Sciencesvol 1 pp 8ndash11 2011
[26] M Revanasiddappa T Suresh S Khasim S C RaghavendrayC Basavaraja and S D Angadi ldquoTransition metal complexesof 1 4(21015840-hydroxyphenyl-1-yl) di-imino azine synthesis char-acterization and antimicrobial studiesrdquo E-Journal of Chemistryvol 5 no 2 pp 395ndash403 2008
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
![Page 4: Research Article Synthesis, Characterization, and ...downloads.hindawi.com/journals/jchem/2013/479343.pdfcm 1 consistent with the iminic absorption of free Schi base [ ]. e band for](https://reader034.fdocuments.net/reader034/viewer/2022050101/5f40419557383b1ae3684685/html5/thumbnails/4.jpg)
4 Journal of Chemistry
M = Mn2+ Co2+ Ni2+ Cu2+ Zn2+
n
N
N
O
HO
OH
O
M
M
Figure 1 Structure of the polymeric compounds
4 Conclusion
From the characterization of ligand and complexes usingCHN analysis IR and NMR structures of ligand and com-plexes were proposed Measurements of inhibition zones ofligand and complexes at different concentrations show thatall complexes have enhanced bactericidal activity more thanligand
References
[1] A S Shakeel N V Kalyane S R Karjgi and M L AhmedldquoSynthesis and antibacterial activity of new Schiff rsquos basesrdquoInternational Journal of Pharmacy and Life Sciences no 5 pp246ndash249 2010
[2] R Johari G Kumar and S Singh ldquoSynthesis and antibacterialactivity of M (II) Schiff base complexrdquo Journal of the IndianCouncil of Chemists vol 26 pp 23ndash27 2009
[3] J H Pandya and M K Shah ldquoSynthesis and antimicrobialproperties of transition metal complexes of novel Schiff baseligand derived from 5-bromosalicyldehyderdquo Journal of theIndian Council of Chemists vol 26 no 2 pp 109ndash112 2009
[4] S Varghese and M K Muraleedharan Nair ldquoSpectroscopicand antimicrobial studies of some 2-hydroxybenzilidene-3-aminophenol complexesrdquo Research Journal of PharmaceuticalBiological and Chemical Sciences vol 1 no 2 pp 347ndash353 2010
[5] S Kumar D N Dhar and P N Saxena ldquoApplications of metalcomplexes of Schiff bases-a reviewrdquo Journal of Scientific andIndustrial Research vol 68 no 3 pp 181ndash187 2009
[6] F M Morad M M E L Ajaily and S Ben-Gweirif ldquoPrepara-tion physical characterization and antibacterial activity of Ni(II) Schiff base complexrdquo Journal of Science and Its Applicationsvol 1 pp 72ndash78 2007
[7] P Singh and R K S Dhakarey ldquoSynthesis characterizationand antimicrobial studies of metal complexes with Schiff basesderived from 2-thienyl glyoxalrdquo Rasayan Journal of Chemistryvol 2 no 4 pp 869ndash874 2009
[8] J Salimon N Salih E Yousif A Hameed and H IbraheemldquoSynthesis characterization and biological activity of Schiffbases of 2 5-dimercapto-134-thiadiazolerdquo Australian Journalof Basic and Applied Sciences vol 4 no 7 pp 2016ndash2021 2010
[9] K S S Lamani O KotreshM A Phaniband and J C KadakolldquoSynthesis characterization and antimicrobial properties ofSchiff bases derived from condensation of 8-formyl-7-hydroxy-4-methylcoumarin and substituted triazole derivativesrdquo E-Journal of Chemistry vol 6 supplement 1 pp S239ndashS246 2009
[10] A M Hamil K M Khalifa A Al-Houni and M M El-AjailyldquoSynthesis spectroscopic investigation and antiactivity activityof Schiff base complexes of cobalt (II) and copper (II) ionsrdquoRasayan Journal of Chemistry vol 2 no 2 pp 261ndash266 2009
[11] A P Mishra and N Sharma ldquoSynthesis characterization X-ray and thermal studies of some Schiff base metal complexesrdquoJournal of the Indian Council of Chemists vol 26 pp 125ndash1292009
[12] T Rosu S Pasculescu V Lazar C Chifiriuc and R CernatldquoCopper(II) complexes with ligands derived from 4-amino-23-dimethyl-1-phenyl-3-pyrazolin-5-one synthesis and biologicalactivityrdquoMolecules vol 11 no 11 pp 904ndash914 2006
[13] N S Gwaram H M Ali M A Abdulla et al ldquoAntibacterialevaluation of some Schiff bases derived from 2-acetylpyridineand their metal complexesrdquo Molecules vol 17 no 5 pp 5952ndash5971 2012
[14] K T Joshi AM Pancholi K S Pandya and A SThakar ldquoSyn-thesis characterization and antibacterial activity of novel Schiffbase derived from 4-acetyl-3-methyl-1-(4rsquo-Methyl-Phenyl)-2-Pyrazolin-5-one and its transition metal complexesrdquo Interna-tional Journal of Research in Chemistry and Environment vol1 no 2 pp 263ndash269 2011
[15] A P Mishra R Mishra R Jain and S Gupta ldquoSynthesisof new VO(II) Co(II) Ni(II) and Cu(II) complexes withisatin-3- chloro-4-floroaniline and 2-pyridinecarboxylidene-4aminoantipyrine and their antimicrobial studiesrdquo The KoreanSociety of Mycology vol 40 no 1 pp 20ndash26 2012
[16] A Prakash M P Gangwar and K K Singh ldquoSynthesis spec-troscopy and biological studies of nickel (II) complexes withtetradentate Schiff bases having N
2O2donor grouprdquo Journal of
Developmental Biology and Tissue Engineering vol 3 no 2 pp13ndash19 2011
[17] A S Munde A N Jagdale S M Jadhav and T K ChondhekarldquoSynthesis characterization and thermal study of some tran-sition metal complexes of an asymmetrical tetradentate Schiffbase ligandrdquo Journal of the Serbian Chemical Society vol 75 no3 pp 349ndash359 2010
[18] U K Singh S N Pandeya S K Sethia et al ldquoSynthesisand biological evaluation of some sulfonamide Schiff rsquos basesrdquoInternational Journal of Pharmaceutical Sciences and DrugResearch vol 2 no 3 pp 216ndash218 2010
[19] N Raman J DhaveethuRaja andA Sakthivel ldquoSynthesis spec-tral characterization of Schiff base transition metal complexesDNA cleavage and antimicrobial activity studiesrdquo Journal ofChemical Sciences vol 119 no 4 pp 303ndash310 2007
[20] V ReddyN Patil and S D Angadi ldquoSynthesis characterizationand antimicrobial activity of Cu(II) Co(II) and Ni(II) com-plexes with O N and S donor ligandsrdquo E-Journal of Chemistryvol 5 no 3 pp 577ndash583 2008
Journal of Chemistry 5
[21] K Nakamato Infrared Spectra of Inorganic and CoordinationCompounds John Wiley New York NY USA 1970
[22] S Joshi V Pawar and V Uma ldquoSynthesis characterization andbiological studies of Schiff bases metal complexes Co (II) Zn(II) Ni (II) and Mn (II) derived from amoxicillin trihydratewith various aldehydesrdquo International Journal of Pharma andBio Sciences vol 2 no 1 pp 240ndash250 2011
[23] J T Makode and A S Aswar ldquoSynthesis characterizationbiological and thermal properties of some new Schiff basecomplexes derived from 2-hydroxy-5-chloroacetophenone andS-methyldithiocarbazaterdquo Indian Journal of Chemistry A vol43 no 10 pp 2120ndash2125 2004
[24] A K Mapari and K V Mangaonkar ldquoSynthesis characteri-zation and antimicrobial activity of mixed Schiff base ligandcomplexes of transition metal (II) ionsrdquo International Journalof ChemTech Research vol 3 no 1 pp 477ndash482 2011
[25] P Venkatesh ldquoSynthesis charecterisation and anti microbialactivity of various Schiff base complex of zinc(II) and copper(II) ionsrdquo Asian Journal of Pharmaceutical and Health Sciencesvol 1 pp 8ndash11 2011
[26] M Revanasiddappa T Suresh S Khasim S C RaghavendrayC Basavaraja and S D Angadi ldquoTransition metal complexesof 1 4(21015840-hydroxyphenyl-1-yl) di-imino azine synthesis char-acterization and antimicrobial studiesrdquo E-Journal of Chemistryvol 5 no 2 pp 395ndash403 2008
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
![Page 5: Research Article Synthesis, Characterization, and ...downloads.hindawi.com/journals/jchem/2013/479343.pdfcm 1 consistent with the iminic absorption of free Schi base [ ]. e band for](https://reader034.fdocuments.net/reader034/viewer/2022050101/5f40419557383b1ae3684685/html5/thumbnails/5.jpg)
Journal of Chemistry 5
[21] K Nakamato Infrared Spectra of Inorganic and CoordinationCompounds John Wiley New York NY USA 1970
[22] S Joshi V Pawar and V Uma ldquoSynthesis characterization andbiological studies of Schiff bases metal complexes Co (II) Zn(II) Ni (II) and Mn (II) derived from amoxicillin trihydratewith various aldehydesrdquo International Journal of Pharma andBio Sciences vol 2 no 1 pp 240ndash250 2011
[23] J T Makode and A S Aswar ldquoSynthesis characterizationbiological and thermal properties of some new Schiff basecomplexes derived from 2-hydroxy-5-chloroacetophenone andS-methyldithiocarbazaterdquo Indian Journal of Chemistry A vol43 no 10 pp 2120ndash2125 2004
[24] A K Mapari and K V Mangaonkar ldquoSynthesis characteri-zation and antimicrobial activity of mixed Schiff base ligandcomplexes of transition metal (II) ionsrdquo International Journalof ChemTech Research vol 3 no 1 pp 477ndash482 2011
[25] P Venkatesh ldquoSynthesis charecterisation and anti microbialactivity of various Schiff base complex of zinc(II) and copper(II) ionsrdquo Asian Journal of Pharmaceutical and Health Sciencesvol 1 pp 8ndash11 2011
[26] M Revanasiddappa T Suresh S Khasim S C RaghavendrayC Basavaraja and S D Angadi ldquoTransition metal complexesof 1 4(21015840-hydroxyphenyl-1-yl) di-imino azine synthesis char-acterization and antimicrobial studiesrdquo E-Journal of Chemistryvol 5 no 2 pp 395ndash403 2008
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
![Page 6: Research Article Synthesis, Characterization, and ...downloads.hindawi.com/journals/jchem/2013/479343.pdfcm 1 consistent with the iminic absorption of free Schi base [ ]. e band for](https://reader034.fdocuments.net/reader034/viewer/2022050101/5f40419557383b1ae3684685/html5/thumbnails/6.jpg)
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
