Diagnosis, structure, and in vitro antimicrobial and antifungal evaluation of some amino benzoic acids, derived ligand schiff base and their mixed complexes with Cu(II), Hg(II), Mn(II), Ni(II) and Co(II)

Article abstract of DOI:10.13005/ojc/340263

Innovative various Schiff bases and their Co(II), Ni(II) and Cu(II) and Hg(II) complexes made by the condensation of 4-amino antipyrine with derived aminobenzoic acid (2-aminobenzoic acid, 3-aminobenzoic acid, and 4-aminobenzoic acid ) have been prepared by conventional approaches. These complexes were studied by magnetic sensibility analysis, FTIR spectra, and molar-conductance and elemental analysis.Analytical values appeared which the mixed-ligand complexes presented ratio about 2:1 (ligand: metal) with the chelation 4 or 6. The prepared compounds offered a good effect on the organisms; bacteria Staphylococcus aurous, Escherichia coli and fungi C.Albicans, A. Niger. etc, the biological products signalize which the mixed complexes show objectively worthy performance compared to all the investigated bacterial strains, and generally the action order of the produced complexes has been characterized as Ni(II) > Cu(II) > L.

Full text of DOI:10.13005/ojc/340263

ISSN: 0970-020 X
CODEN: OJCHEG
2018, Vol. 34, No.(2):
Pg. 1105-1113
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Diagnosis, Structure, and In vitro Antimicrobial and Antifungal
Evaluation of some Amino benzoic acids, derived Ligand
Schiff base and their Mixed Complexes with Cu(II), Hg(II),
Mn(II), Ni(II) and Co(II)
REHAB KADHEM RAHEM AL-SHEMARY1*,LEKAA KHALID ABDUL KAREM1
and FAAZA HASEEN GHANIM
Department of Chemistry, College of Education for Pure Sciences, Ibn -Al-Haitham,
University of Baghdad, Adhamiyah, Baghdad,10001, Iraq.
Corresponding author E-mail: drrehabalshemary@gmail.com
http://dx.doi.org/10.13005/ojc/340263
(Received: October 05, 2017; Accepted: January 30, 2018)
ABSTRACT
Innovative various Schiff bases and their Co(II), Ni(II) and Cu(II) and Hg(II) complexes
made by the condensation of 4-amino antipyrine with derived aminobenzoic acid (2-aminobenzoic
acid, 3-aminobenzoic acid, and 4-aminobenzoic acid ) have been prepared by conventional
approaches. These complexes were studied by magnetic sensibility analysis, FTIR spectra, and
molar-conductance and elemental analysis. Analytical values appeared which the
mixed-ligand complexes presented ratio about 2:1 (ligand: metal) with the chelation 4 or 6. The
prepared compounds offered a good effect on the organisms; bacteria Staphylococcus aurous,
Escherichia coli and fungi C. albicans, A. niger. etc, the biological products signalize which the
mixed complexes show objectively worthy performance compared to all the investigated bacterial
strains, and generally the action order of the produced complexes has been characterized as
Ni(II) > Cu(II) > L.
Keywords: Schiff bases, 4-aminopyrine, Biological activity.
INTRODUCTION
been formidable attention in the composition of new
bioactive amines and evolving effective processes
for their derivatives.4-6 Derivatives of 4-amino
antipyrine are used as the opener organic
intermediates for the preparation of biomolecules
for synthetic purposes, possess important
biological, catalytic activity and an efficient reagent
in trace analysis of some metal cations.6-7 The
Through the previous decades, Schiff
base was the most significant ligand in the
chemistry of the metal complexes to include donor
atoms like nitrogen and others.1-3 considering their
great enforcements in the scope of bioorganic,
synthetic organic and medical chemistry, there has
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RAHEM AL-SHEMARY et al., Orient. J. Chem., Vol. 34(2), 1105-1113 (2018)
coordinating properties of 4-aminoantipyrine have susceptibility measuring has acquired on the solid
been amended to give new ligands composed by state using Bruker BM6 instrument. Micro analysis
the reaction with ketones, carbazides, (C, H and N %) of the formed complexes had
thiocarbazides, and aldehydes etc.8-10 such as performed by means of C.H.N. Analyzer on Perkin
anthranilic acid, vanillin, furfural and o-phenylene Elmer 2400 sequence II. Dissolving details that
diamine.11-14 The chelation chemistry, biological evaluated in Gallen Kamp melting point apparatus
efficacy and new structural lineaments of the Schiff were unmodified.
bases have attracted attention. They are contain
potential chelation positions about four with various
chelating force also this can allow altitude to different
Synthesis of ligands
The ligands [A1], [A2] and [A3] were
synthesis approving to the general technique
linking and several stereo-chemical in their
displayed in (scheme 1 ,2 and 3).The[A1], [A2] and
chelation complexes.15-17 In this research, we
[A3] was synthesized bymixing an ethanolic solution
characterized the installation and description of and
(15 mL) of 4-amino antipyrine (0.203 g, 0.001m
the mixed coordination complexes of the ligands
mole) with (0.012g, 0.001m mole) 2-aminobenzoic
(Schiff bases and 1,10-phenanthroline) with several
acid in the same volume of ethanol (four drops of
metal ions.
glacial acetic acid have been added). This reaction
has been subsequently refluxed with stirring for 8h
and the solution has been tolerable at room
MATERIALS AND METHODS
temperature to form [A1, A2 and A3].
Apparatus and reagents
All
reagents
4-aminoantipyrine,
For (A1) (C18H18N4O2) Mwt: (322.36),
Yield(78%) : 66 : m.p.: 156°C, Anal. Cal. (%): C, 67.07;
H, 5.63; N, 17.38, Found (%): C, 66.71; H, 5.32; N,
17.11, IR (KBr,cm-1): 3423,υ (OH); 3350, 3223,
2-aminobenzoic acid, 3-aminobenzoic acid,
4-aminobenzoic point out acid, nickel cobalt,
mercury in addition to copper (II)chlorides were of
Merck & Co. results and utilized as provided
13C and 1HNMR spectra . Microanalytical data of the
complexes had measured at Bruker specrospin
ultra shield magnets 300 MHz instruments. FTIR
spectra was registered on a Shimadzu FTIR
spectrophotometer 8300. UV/Vis spectra were noted
on UV/Vis Varian Uv-Cary-100 spectrophotometers.
The chloride content registered by way
(potentiometric titration) on 686-Titro Dosim
A-Metrohm Processor-665 /Swiss. Magnetic
υas,s(NH);3016,(C%H)aromitic;2908,(C%H)alphatic;1686,(C=O);
1606 ,(C=N)st;1529,(C=C)st,UV-Vis(DMSO,λmax
(nm)(cm-1)):240(41666),312(32051) ,1HNMR
(DMSO-d6,300MHZ) δ:2.26, (s,3H,CH3); 2.49,
(s,6H,DMSO);3.38,(s,3H,CH3); 5.17, (s,2H,
NH2);6.54-8.12,(m,12H8,C6H5); 12.85, (s,1H,
COOH).13CNMR(DMSO,75MHZ)λ:9.14(s,C-
CH3);33.7(s,N-CH3):41.01; (s, DMSO), 114.18(s, =C-N);
123.56-135.45 (m,C6H5); 151.17 (s,C=N);154.98
(s,N-C=); 161.72(s, COOH)
O
NH2
H3C
NH2
H3C
C
OH
O
HO
C
NH2
N
N
O
N
H3C
H3C
N
N
+
reflex 8hrs.
Ethanol/HAA
scheme 1
For (A2) (C18H18N4O2) Mwt: (322.36), (C%H)aromatic;2929,(C%H)aliphatic;1660,(C=O)carboxylic;1576,
Yield(%): 89, Anal. Cal. (%): C, 65.24; H, 5.78; N, (C=N)imine; 1543,(C=C)aromatic, UV-Vis(DMSO,
16.91, Found (%): C, 63.67; H, 4.40; N, 9.21, IR
(KBr,cm-1) :3478,υ(O-H);3327,3236, υas,s(NH);3075, (DMSO-d6,300MHZ): δ:2.26, (s,3H,CH3); 2.47,
δ
max(nm)(cm-1)): 275 (36363), 385 (25839).1HNMR

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(s,6H,DMSO);3.58,(s,3H,CH3); 5.47, (s,2H,
NH2);6.14-8.02, (m,12H,C6H5) ;12.58,(s,1H,OH).
13CNMR (DMSO,75MHZ) δ: 10.12 (s,C-CH3)
;33.7(s,N-CH3):40.38; (s,DMSO), 114.18(s,=C-N);
123.56-149.97 (m,C6H5); 151.17 (s,C=N);154.26
(s,N-C=);161.89(s, COOH).
O
NH2
H3C
NH2
H3C
C
OH
HO
N
N
N
C
O
H3C
N
O
H3C
N
reflex 8hrs.
+
NH2
Ethanol/HAA
scheme 2
For (A3) (C18H18N4O2) Mwt: (322.36), Colour:
(yellow) Yield(%) : 85 : m.p.: 232°C, Anal. Cal. (%):
C, 67.07; H, 5.63; N, 17.38, Found (%): C, 67.97; H,
5.88; N, 17.69, IR (KBr, cm-1): 3444
(DMSO-d6, 300MHZ):λ: 2.26,(s,3H,CH3);2.47,(s,6H,
DMSO); 3.11(s,3H ,CH3); 4.95 (s,2H ,NH2); 6.5-8.12,
,
,
(m,12H,C6H5); 12.83, (s,1H,OH). 13C NMR
(DMSO,75MHZ) λ: 10.12 (s,C-CH3) ;33.7 (s,N-CH3):40.38;
(s,DMSO), 106.14 (s,=C-N); 123.56-149.97
(m,C6H5); 151.17 (s,C=N);154.26 (s,N-C=); 165.64(s,
COOH).
υ(OH);3336,3215, υas,s(NH); 3051,(C%H)aromatic
;
2970,(C%H)aliphatic; 1668, (C=O) carboxylic ; 1579(C=N)
;1566,(C=C) aromatic,UV-Vis (DMSO, δmax
imine
(nm)(cm-1): 267 (37453), 350(28571).1HNMR
NH2
H3C
O
NH2
H3C
C
OH
N
O
C
N
H3C
N
N
O
H3C
N
OH
+
reflux 34hrs.
Ethanol/HAA
NH2
scheme 3
3021,(C%H)
; 2927,(C%H) alphatic; 1545υasy
Syntheses of the mixed -complexes
aromitic
.(COO-);1592, (C=N)st ;1518, (C=C)st;1445 υsy.
(COO-) 565, (M%N)st,UV-Vis (DMSO, δmax (nm)
(cm-1)):258, (38759); 292,(34246); 379, (26364);
656,(15242);764,(13087),Molar conductance
(DMSO): 8.9 S. mol −1.cm 2 , μeff (BM): 2.72
(0.002 mmol , 0.436) g ligands [A1],
[A2]and [A3] in KOH (0.001 mmol, 0.056 g) solution
and metal salts (0.340 g CuCl2.2H2O, 0.543 g HgCl2
0.475 g, CoCl2.6H2O,0.475 g NiCl2.6H2O and
0.395 g MnCl2.4H2O) (0.001 mmol) with 1,10-
phenanthroline (0.001 mmol ,0.18 g)were dissolved
in(15 mL) ethanol then for 1.5 h reflux the mixture.
Then, the item was categorized at that point cleaned
with (2:5) mL ethanol: diethyelther and dried at room
temperature. At similar method were obtained the
other complexes.
For [Cu(A1)(PHN)Cl] (C30H25ClCuN6O2)
(S2);Mwt:(600.56), Yield(%):77 , m.p.:218 °C Anal.
Cal. (%): Cu, 10.58; C, 60.00; H, 4.20; N, 13.99; Cl,
5.90. Found (%): Cu, 10.69; C, 50.34; H, 6.11; N,
19.17; Cl, 12.38.IR (KBr, cm-1): 3478,υ(O-H);
3424,3449,(NH2)st;3038,(C%H)aromitic;2933,
(C%H)alphatic; 1621, (C=N)st ;1525,υasy.(COO-)
;1516,(C=C)st; 1417, υsy.(COO-);559,(M%N)st,
UV-Vis (DMSO, δmax (nm) (cm-1)): 254,(39370);
286, (34965); 682,(14662).Molar conductance
(DMSO): 10.2 S. mol -1. cm2, μeff(BM): 1.86
For [Ni(A1)(PHN)Cl] (C30H25 ClN6NiO2)
(S1);Mwt: (595.70), Yield(%:68, m.p.: 267 °C ,Anal.
Cal. (%): Ni, 9.85; C, 60.49; H, 4.23; N, 14.11; Cl,
12.52, Found (%): Ni, 9.85; C, 60.49; H, 4.23; N,
19.67; Cl, 12.20, IR (KBr,cm-1): 34203, 3352,(NH2)st;

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RAHEM AL-SHEMARY et al., Orient. J. Chem., Vol. 34(2), 1105-1113 (2018)
N
CH3
N
C
N
O
O
CH3
NH2
Cl
M
N
N
II
M =
Ni& Cu
For[Ni(A2)(PHN)Cl2] (C30H26Cl2N6NiO2);
For [Cu(A2)(PHN)Cl2] (C30H26Cl2 CuN6O2)
(S4); Mwt: (637.02), Yield(%):77, m.p.: 218 °C Anal.
Cal. (%): Cu, 9.98; C, 56.56; H, 4.11; N, 13.19; Cl,
11.13. Found (%): Cu, 10.69; C, 50.34; H, 6.11; N,
19.17; Cl, 12.38.IR (KBr, cm-1) 3481,υ(O-H); 3429,
3368 (NH2)st ;3062,(C%H) aromitic ; 2923,(C%H) alphatic
Mwt:(632.17), Colour:(Greenish yellow),Yield(%:68
, m.p.: 267 °C ,Anal. Cal. (%): Ni, 9.28; C, 57.00; H,
4.15; N, 13.29; Cl, 11.22, Found (%): Ni, 10.23; C,
50.29; H, 6.11; N, 19.67; Cl, 12.20, IR (KBr, cm-
1):3464,υ(O-H); 3420, 3352 ,(NH2) st;3096,
(C%H)
; 2835,(C%H) alphatic; 1705, (C=O)st ;
aromitic
1621,(C=O)asymm; 1585 (C=N)st 1421,(C=O)symm
;
16201590 (C=N)st 1618, (C=C)st ; 565, (M%N)st,
UV-Vis (DMSO, δmax (nm) (cm-1)): 258, (38759); 292,
(34246); 379, (26364); 656, (15242); 764,
1585, (C=C)st; 1171,(C-O)st 523,438 (M%N)st,
UV-Vis (DMSO, δmax (nm) (cm-1)):254, (39370);286,
(34965); 413, (24213); 982, (10176).Molar conductance
(DMSO): 10.2 S. mol −1. cm2, μeff(BM): 1.68
(13087),Molar conductance (DMSO): 8.9 S. mol −1
cm 2, μeff (BM): 2.72
.
11.22,.Found (%): Ni, 9.56; C, 57.88; H, 4.34; N, 13.28;
For [Ni(A3)(PHN)Cl2] (C30H26N6Cl2NiO2)
(S5); Mwt: (632.17), Yield(%:70, m.p.: 218 °C ,Anal. Cl, 11.56, IR (KBr, cm-1):3458,υ(O-H); 3420, 3352
Cal. (%): Ni, 9.28; C, 57.67; H, 4.15; N, 13.29; Cl,
,(NH2)
3021 ,(C%H)
; 2927,(C%H)
;
alphatic
st;
aromitic

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RAHEM AL-SHEMARY et al., Orient. J. Chem., Vol. 34(2), 1105-1113 (2018)
1624, (C=N)st ;1618, (C=C)st ; 565, (M%N)st,UV-Vis
(DMSO, δmax (nm) (cm-1)): 258, (38759); 292, (34246);
775, (12893),Molar conductance (DMSO): 8.9 S.
mol−1. cm2, μeff (BM): Dia
4.63; N, 14.85. Found (%): Cu, 10.69; C, 50.34; H,
6.11; N, 19.17. IR (KBr, cm-1):3476,υ(O-H);3424,
3449,(NH2)st;3038,(C%H)aromitic; 2933,(C%H)alphatic
;
1621, (C=O)st 1621, (C=N)st ;1516, (C=C)st; 559,
(M%N)st,UV-Vis(DMSO, δmax (nm) (cm-1)): 254,
(39370); 286, (34965); 543,(18416) . Molar
conductance (DMSO): 10.2 S. mol−1. cm2, μeff(BM):
1.78
For [Cu(A3)(PHN)Cl2] (C30H26CuN6O2)
(S6); Mwt: (566.11), Colour: (Green), Yield(%) : 77 ,
m.p.: 218 °C Anal. Cal. (%): Cu, 11.22; C, 63.65; H,
Biological studies
combination of the shift base ligands with metallic
ion. A wide spectrum at 3423 cm-1, 3478 cm-1 and
3444 cm-1 owing to υ(OH) stretching vibration for
Al, A2, and A3, respectively, υasym, symNH2 stretching
vibration for Al, A2, and A3, respectively. Also, they
showed at 1636 while this band was disappeared
in the spectrum of its mixed complexes for A1.
In addition displayed at (3358, 3223) cm-1,
(3327, 3236) cm-1, and (3336, 3215) characteristics
of thestretching mode (azomethine) (C=N)
suggesting the forming of the ligand results. This
frequency was moved to lower value in the spectrum
of its metal complexes (1581–1565 cm-1) liken with
the ligand signalizing the partnership of the nitrogen
of azomethine in coordination with metal ion. The
chelation of nitrogen to the metallic ion could be
prospective to lessen the electron density of the
imine connection and consequently triggered a
change in the group of (C=N). The penetrating
bands at 1686 cm-1,1668cm-1 and 1660 cm-1 shows
in the IR spectra of the free ligands Al, A2, and A3
may be allocated to the υ(C=O)(carboxylic cluster).
On the other hand, all spectra compounds forAl
have stated the nonappearance of the characteristic
band with the presence of dual characteristic bands
The organic action (In vitro) of selected
compounds was screened with two bacteria
Staphylococcus aureus and Escherichia coli by disc
expansion way by means of nutrient agar as the
environment and control as streptomycin. Also the
antifungal efficacy of the components was screened
by the same previous way in the environment as
potato dextrose agar with the fungi A. niger and
C. albicans. All the components have been in the
(25, 50 and 100 ppm) concentrations of DMSO
solutions that have synthesized disjointedly. A well
was got on agarenvironment in the cultivated micro
organism in a typical procedure. It was loaded with
the screen solution utilizing plate and a micropipette
the was brood for bacteria at 24 h , 37 °C and for
fungi at 72 h 30 °C. Investigational solution was
growth and suffused of the inoculated micro
organism was influenced during this interval. The
inhibition region advanced, at that was noted the
concentration.
IR spectra
IR spectra of the Ligands and mixed
compounds obviously point out the bonding

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RAHEM AL-SHEMARY et al., Orient. J. Chem., Vol. 34(2), 1105-1113 (2018)
at 1545–1525 and 1445 –1417cm-1 related to υasy. inaccurate octahedral arrangement in the metal.This
(COO-) in addition to υsy.(COO-) correspondingly, structure is additionally reinforced by its magnetic
(Δυ(COO”)=υsy.(COO”)-υsay.(COO”)) in range susceptibility data (1.86 lB).
(108-100) cm-1,indicated the involvement of
deprotonated group of (COOH) in bonding and an
The spectrum of complex (S5) of the
organization of metallic ions through oxygen atoms displayed one d-d transition band at 12893 cm-1
of carboxyl groups signifying the contribution of the that belong to 1A1g(F) → Eg transition.The transition
2
carboxylate oxygen atom in the compound structure. corresponds to a square planar of the compound
Decisive indication of the bonding was similarly has geometry that is likewise confirmed by its
exposed noticeably that innovative bands in all diamagnetic susceptibility.The absorption spectrum
metal complex spectrums in the small frequency of the complex (S6) presented the d–d bands at
2
regions at 548–531 and 483–465 cm-1 present to 18416 cm-1.This corresponds to 2B1g→ A1g transition.
υ(M–O) and υ(M–N) extending frequencies, This d–d transition has a square 2D arrangement.
separately, which weren’t appeared in the spectrum This structure is then confirmed by its magnetic
of ligands.
susceptibility data (1. 78 lB).
Electronic spectra
NMR spectra
UV-Vis of [A1], [A2] and [A3] ligands spectra
1HNMR spectrum of Schiff base [A1]
and the mixed-complexes were determined in (in DMSO-d6 as solvent), showed a singlet signal
solution of DMSO. Each compound was displayed at δ2.26 ppm for three protons of CH3 group, singlet
huge energy band in the range 4166 -36363 cm-1. signal at 2.49ppm for 6 protons for DMSO, a singlet
This can be assigned to the L.F band. Also, the high signal at δ3.38 ppm for three protons of CH3 group,
energy absorption band in 25839–34965 cm-1 range. milt signals in range δ(6.54-8.12) ppm that might
This can be assigned to the C.T band. The (S1) be due to the twelve aromatic protons of phenyl
complex spectrum displayed three d–d transition rings. And two protons at NH2of amine group gives
bands at 26364, 15242 and 13087 cm-1 that is due as a broad singlet signal at δ5.17 ppm.Finally, singlet
3
3
3
3
3
to A2g(F)→ T1g(F),3A2g(F)→ T2g(F) and A2g(F)→ T1g(P) signal at δ(12.85) ppm concerning one proton of
arrangements, individually, distinguishing of an OH carboxylic group.
octahedral arrangement. This arrangement has
1HNMR spectrum of Schiff base [A2]
been moreover confirmed by its magnetically
sensibility data (2.72lB)
(in DMSO-d6 as solvent), showed a singlet signal at
δ2. 26 ppm for three protons of CH3 group, a singlet
signal at 2.47 ppm for 6 protons for DMSO, also
singlet signal at δ3.58 ppm for three protons of CH3
group, milt signals in range δ(6.14- 8.02) ppm that
might be due to the twelve aromatic protons of
The complex (S2) spectrum showed the
d–d bands at 14662 cm-1. This corresponds to
2Eg(F)→ T2g(F) transition.The d–d transition facilitates
2
an unrecognizable octahedral arrangement in the
area metal. Accordingly, the design is more
confirmed by its magnetically susceptibility
magnitude (1.86 lB).
phenyl rings, and two protons at NH2of amine group
gives as a broad singlet signal at δ4.47 ppm. Finally,
a singlet signal at δ(12.58)ppm relating to one proton
of OH carboxylic cluster.
The complex (S3) spectrum presented
1HNMR bands of Schiff base [A3]
dual d-d transition bands in 15242 region, (in DMSO-d6 as solvent), Fig. (9) showed a singlet
3
3
and 13087cm that are given to A2g(F)→ T1g(P) and signal at δ2. 26 ppm for three protons of CH3 group,
3
3A2g(F)→ T1g(F)transitions, correspondingly. These singlet signal at 2.47 ppm for 6 protons for DMSO, a
transitions characterize the octahedral structure of singlet signal at δ3.11 ppm for three protons of CH3
the compound, that is as well confirmed by its group, milt signals in range δ(6.5- 8.12) ppm that
magnetically susceptibility magnitude (4.45 lB).The might be due to the twelve aromatic protons of
absorption spectrum of the complex (S4) presented phenyl rings, and two protons at NH2of amine group
the d–d bands at 14662 cm-1. This corresponds to gives as a broad singlet signal at δ4. 95 ppm.Finally,
2
2Eg(F)→ T2g(F) transition. This d–d transition has an a single signal at δ(12.83) ppm for carboxylic proton

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The 13CNMR ligand (A1) band displayed
theCH3-C= group as the signal at 9.12 ppm and
CH3-N= group at 33.85 ppmgroup. Also, the peak
of (=C-N) group showed at 105.18 ppm. The other
peaks of aromatic carbons resonance observed at
122.70-149.97 ppm. The signals at 151.17 ppm.
The other peaks of aromatic carbons resonance
observed at 123.57-149.97ppm. Also, the peak of
carboxylic carbon is displayed at 165.27.
of their ethanolic solution. The molar conductivity
values of (S1), (S2), (S3) and (S4) under
investigation are found to be at (72, 76, 83,87, and
89 ohm-1 cm2 mol-1), correspondingly. It is clear from
these data that the compounds are ionic and they
are of 1:2 electrolytes in type20. In addition, the
conductance data are low for (S5) and (S6)
complexes lie at(1.2 and 2.9 ohm-1 cm2 mol-1)
support their non-electro nature of the compounds.
The 13CNMR ligand (A2) spectrum
displayed theCH3-C= group as the signal at 10.12
ppm andCH3-N= group at 33.85 ppmgroup iminic
carbon (C=N) as functional group signal at 106.08
ppm. The other peaks of aromatic carbons
resonance observed at 123.57-149.97 ppm.
Also the peak of 10.12 (s,C-CH3);33.7
(s,N-CH3):40.38;(s,DMSO), 106.14(s,=C-N);
123.56-149.97 (m,C6H5); 151.17 (s,C=N);154.26
(s,N-C=); 165.64(s, COOH).
Biological activities
The Biological activity In vitro of created
Schiff base ligands and their resultant metal
compounds on tested two bacteria S. aureus and
E. coli and dual fungi A.niger and C. albicans was
done. Each particular components presented
perfect biological effectiveness with micro-
organisms. The biological effectiveness of all
selected compounds were liken with the norm
fungicide and bactericide. The mixed complexes
have mild effectiveness were liken to the typical
degrees. Nevertheless, all compounds are more
effective as compared with their relevant ligands. It
is, on the other hand, identified that chelation is
likely to make Schiff bases have more influential
and strong bactereostatic agents, hence
constraining the growing fungi and bacteria more
than the parent ligands. It is doubted that agents
like dipole, conductivity, moment solubility and cell
penetrability technicality (affected by the existence
of metallic ions) can be probable causes
intensification in efficiency. The diameter in (mm)
of the repression domains are summarized in
Tables 1 and 2.
The 13CNMR ligand (A3) spectrum
displayed theCH3-C= group as the signal at 10.12
ppm and CH3-N= group at 33.85 ppm, also, the
peak of (=C-N) group showed at 106.14 ppm. The
other peaks of aromatic carbons resonance
observed at 123.57-149.97 ppm. The signals at
151.17-154.26 ppm of ionic carbon (C=N) and
(N-C=) as functional groups. Also, the signal of
carboxylic carbon is displayed at 165.64.
Molar conductivity
The molar conductivities of the compounds
had measured at room temperature under 10-3 M
Table 1: Antibacterial screening data for the ligands and their compounds
Compound
E. coli
S.aureus
Diameter of inhibition % Activity index
zone (mm)
Diameter of inhibition
zone (mm)
% Activity
index
25
10
9
50 100
25
49
50
50
78
80
81
84
82
82
50
55
54
56
84
84
86
87
87
86
100 25
50 100 25
50
57
58
59
90
85
98
100
59
60
61
93
[A1]
[A2]
[A3]
[S1]
[S2]
[S3]
[S4 ]
[S5]
12
11
13
20
19
22
24
25
26
22
15
14
16
25
21
27
30
31
28
26
59
57
60
90
88
92
95
91
92
9
11 15
12 16
14 18
19 21
20 22
22 24
24 27
25 28
26 30
52
53
55
87
81
92
97
82
88
10
12
15
16
18
20
19
20
11
17
15
18
19
20
21
21
87
101
104 106
103 105
104 107
[S6]
Streptomycin (Standard)
100 100 100 18
22 26 100 100 100

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RAHEM AL-SHEMARY et al., Orient. J. Chem., Vol. 34(2), 1105-1113 (2018)
Table 2: Antifungal screening data for the ligands and their complexes
Compound
Diameter of inhibition zone (mm); Concentration in ppm
A. niger
C. albicans
25
13
10
19
17
18
19
18
20
22
50
18
17
25
20
22
23
24
22
25
100
21
20
30
25
27
29
31
32
34
25
15
14
18
20
19
21
19
18
20
50
18
17
20
27
25
27
26
30
31
100
24
20
22
34
37
38
36
35
38
[A1]
[A2]
[A3]
[S1]
[S2]
[S3]
[S4 ]
[S5]
[S6]
1
Fig. 1. H-NMR spectrum of the Ligand(L1)
1
Fig. 3. H-NMR spectrum of the Ligand(L2)
Fig. 2.13C-NMR spectrum of the Ligand(L1)
Fig. 4. 13C-NMR spectrum of the Ligand(L2)

1113
RAHEM AL-SHEMARY et al., Orient. J. Chem., Vol. 34(2), 1105-1113 (2018)
1
Fig. 5. H-NMR spectrum of the Ligand(L3)
Fig. 6.13C-NMR spectrum of the Ligand(L3)
CONCLUSION
The biological activity of these metal
compounds with bacteria; E. coli and S. aureus, and
fungi A. niger and C.albicans was investigated. From
the results, it is found that the mixed complexes
have been patterned for the biological testing
mostly regarding the mixed compounds versus the
bacteria and fungi, also, and may be concluded
that the metal complexes are effective both for
bacteria and fungi also.
1
From the UV–Vis H and 13CNMR and IR
spectra, elemental analysis, molar conductivity, and
magnetic values, it is imaginable to measure the
kind of chelation of the ligand in their mixed
complexes. Depended on these values, octahedral
arrangement has been signified as (S1) (S2) (S3)
and (S4) complexes except (S5), (S6) complexes
are assigned a square planar arrangement.
REFERENCES
1.
2.
Dhar, D.N.;Taploo, C.L., J.Sci.Ind.Res., 1982,
41(8), 501-506.
Eur. J. Inorg. Chem., 2004, 47, 10-4717.
Avaji ,P.G.; Kumar, C.H.V., Patil ,S. A,
Shivananda, K.N.;Nagaraju, C., Eur.J. Med.
Chem., doi: 10.101.6 /j.ejmech. 03.032, 2009.
Canpolat, E. and Kaya, M., J. Coord. Chem.,
2004, 123, 413-425
RaheemR K.; Fayad A.A., Sci. Revs. Chem.,
Commun., 2016, 6(3), 37-52.
Chakravarty, A.R., Nreddy, A.P., Santra, B.K.;
Thomas, A.M., J. Indian. Chem. Sci., 2002,
114, 319-401.
Himaja ,M.;Kailash, R.; Anish, K.V.;Ramana,
M.V. ; Karigar, A. A., J. Pham. & Sci.
Innv.,2012,1(1)67-70.
Raheem, R.K.;Tawfiq, M.T., Eur.Chem.Bull.,
2016, 5(11), 470-478.
Ferreira, E.I.; Tavares, L.C., Bioorg. Med.
Chem., 2002, 10, 557-560.
Anand, K; Gupta, S.; Barhate, V.D,Res. J. of
Pharma.Bio. and Chem. Sci., 2012, 3(3)
10103 -10126.
Raman, N. ; Sobha , S.; Mitu, L.; J. Saudi
Chem. Soc., 2013, 17, 151–159.
Sampath, K. ; Karthik, K.; Sivahari R.;Rasayan
J. Chem., 2017, 10(4), 1184-1188.
Prakash, V.; Suresh, M. S.,Res. J. Phar., Bio.
& Chem.Sci., 2013, 4(4), 1536-1550.
13.
Maria, D.M.C.; Ribeiro, D.; Jorge, M.G.; Ana,
L.R.S.;Paula, C.F.C.;Bernd, S., J.Mol.Catal.
A: Chem., 2004, 224, 207-212.
14.
15.
16.
3.
4.
5.
Cotton, A.F.; Wilkenson, G., 5thEdition 1988,
John Wiley and Sons USA., 37-50.
Hassan, K.; Salehzadeh, H.S.; Parish, R.V.,
J. Molecules., 2002, 7, 140-144.
Kirshener, Wei S.Y.K., Francis, D.; Bergman,
J.H., Anticancer and potential antiviral
activity of complex inorganic compounds, J.
Med. Chem., 1966, 9, 369-372.
Joana, C.;Carolina ,M.; Sofia, S.;Pedro,V.B.
; Alexandra, R. F., Ann. Med. Chem. Res.,
2015, 1(2), 1010, 1-5.
17.
6.
18.
19.
20.
7.
8.
Yu, R.; Ling, Z., Cheng-He, Z. ; Rong-Xia, G.,
Med. chem., 2014, 4(9), 640-662.
Kostova, I.; Raleva ,S.; Genova, P. ; Argirova,
R., Bio. Chem., & Appli., 2006, 5, 1–9
Lever A.B.P., Elsevier 1984, New York.
Kojima, M.; Taguchi, H.; Tsuchimoto, M.;
Nakajima, K., Coord. Chem.Rev., 2003,237,
183-196.
9.
10.
21.
22.
23.
11.
12.
Long, N.J., Chem. Int. 1thEdition 1995., 34, 21.
Cusumano, M.; Messina, M.A.; Nicolo F.,
Pietro M.L.D., Rotondo A., and Rotondo, E.,