Synthesis, Physico - Chemical and Antimicrobial

Transactions on Engineering and Sciences
Vol.3, Issue 2, February 2015
ISSN: 2347-1964 (Online) 2347-1875 (Print)
Synthesis, Physico -Chemical and Antimicrobial

Properties of n(II),Fe(II),Co(II),Ni(II),Cu(II),Zn(II)
and Cd (II), Mixed Ligand Complexes of cephalexin
mono hydrate (antibiotics) and Furan-2-carboxylic
acid
Taghreed . Hashim Al-Noor1
1,2&3 Department
Faiza. H Ghanim2
Bassim Abd Shahoobi3
of Chemistry .Ibn -Al-Haithem College of Education for pure science, University of

Baghdad, Baghdad, Iraq.
Abstract A series of new mixed ligand complexes of Mn(II),Fe(II),Co(II),Ni(II),Cu(II),Zn(II) and Cd

(II) have been synthesized with cephalexin mono hydrate ( CephH) = ( C16H19N3O5S.H2O) and
Furan-2-carboxylic acid(FCA H) =( C5H4O3) .The mixed ligand complexes have been
repeated
melting
point
determination,
spectroscopic
spectral
UV-Vis.),molar conductance, magnetic susceptibility measurements and determination

of
the metal
in
the
complexes
by
flame(AAS). The
characterized by
measurements
(FT-IR,
the percentage
ligands and their metal complexes were
screened for their antimicrobial activity against four bacteria (gram + ve) and (gram -ve).The proposed
structure of the complexes using program, Chem office 3D (2006) . The general formula have been
given for the prepared
mixed ligand complexesNa2[M(FCA)3(Ceph)], M(II) = Mn (II) , Fe
(II),Co(II) ,Ni(II),Cu (II), Zn(II) , and Cd(II).

Index Terms Cephalexin antibiotics, Furan 2-carboxylic acid, drugs mixed ligand complexes, and
antibacterial activities.
I. INTRODUCTION
Bioactive donor site of ( N,S/O) atoms in organic ligand moieties were widely used in the
development of metal based drugs, analytical, industrial, medicinal, agricultural, biological and clinical
areas. [1-2].
Many drugs possess modified toxicological and pharmacological properties when they are in the form
of metal complexes. The most widely studied metal in this respect is copper(II) which has proved beneficial
in diseases such as tuberculosis, gastric ulcers, rheumatoid arthritis and cancers. [3].The coordination
chemistry of some beta-lactam antibiotics with transition and d10 metal ions has been reported [4-8].
Furan-2-carboxylic acid( C5H4O3) (FCAH) is a heterocyclic aromatic compound with five- membered ring
structure consisting of four CH2 groups, one oxygen atom and a carboxylic group. [9].Synthesis and
identification of type mixed ligand complexes of
M+2
Ions using Furan-2-carboxylic acid as a primary
ligand and 1,10-phenanthroline (phen )as secondary ligand has been reported. [10].
Literature survey shows that no studies on the synthesis and characterization of mixed ligand
complexes of Furan-2-carboxylic acid and cephalexin (antibiotics) have been reported.
In this paper we present the synthesis and study of Mn(II),Fe(II),Co(II),Ni(II), Cu(II),Zn(II), and Cd(II)
complexes with cephalexin mono hydrate (antibiotics) as a primary ligand and
Furan-2-carboxylic acid
as secondary ligand.
II. EXPERIMENTAL
A. Chemicals : All chemical reagents and solvents used were of analytical grade and were used without
further
purification
and
were
used
as
received
MnCl2.2H2O,
FeCl2.9H2O,CoCl2.6H2O,
Techscripts

NiCl2.6H2O,CuCl2.H2O, CdCl2.H2O, and ZnCl2,KOH (supplied by either Merck or Fluka) ethanol, methanol
dimethylforamaide, and KBr, acetone , benzene, and chloroform
from (B.D.H).Cephalexin powder DSM
(Spain) and Furan-2-carboxylic acid (merck).

B. Instrumentals: UV-Vis spectra were recorded on a (Shimadzu UV- 160A) Ultra Violet-Visible
Spectrophotometer. IR- spectra were taken on a (Shimadzu, FTI R- 8400S) Fourier Transform Infrared
Spectrophotometer (4000- 400) cm-1 with samples prepared as KBr discs. Metal contents of the complexes
were determined by atomic absorption(A.A)technique using a Shimadzu AA 620G atomic absorption
spectrophotometer. The Chloride contents of complexes were determined by potentiometric titration
method using (686-Titro processor-665. Dosimat
10-3M
of complexes in DMF at
25C
Metrohn Swiss). Conductivities were measured for
using (conductivity meter, Jewnwary, model 4070). Magnetic
measurements were recorded on a Bruker BM6 instrument at 298K following the Faradys method. In
addition melting points were obtained using (Stuart Melting Point Apparatus). The proposed molecular
structure of the complexes was drawing by using chem. office prog, 3DX (2006).
C. General synthesis of the mixed ligands metal complexes: A general method was used for the synthesis of the
metal complexes .A solution of Furan-2-carboxylic acid (0.336 gm, 3 m mol) in 50% (v/v) ethanol water (10
ml) containing potassium hydroxide (0.168, 3mmol) and a solution of
cephalexin mono hydrate (0.347
gm ,1 m mol) in 50% (v/v)ethanolwater (10 mL) containing potassium hydroxide (0.056,1mmol)were

added simultaneously to
a solution of MCl2.nH2O (1 m mol) in 50% (v/v)
ethanol water, (10 mL) in the
stoichiometric ratio.[3FCA- : M: ceph-] ( Scheme 1).The above solution was stirred for 1-houre
to stand for overnight .the product formed was filtered off ,washed several times with
ethanol water to remove any traces of the un reacted starting materials and dried
and allowed
hot 50% (v/v)
in air ,and analyzed
employing standard method. [11]

III. RESULTS AND DISCUSSION
A. Characterization of Metal Complexes: Generally, the complexes were prepared by reacting the respective
metal chloride with the ligands using 1:1:3 mole ratios, [M: Ceph:3(FCA)], i.e. one mole of metal chloride :
one mole of
cephalexin and three moles of FCAK . The synthesis of mixed ligand metal complexes may be
represented as follows (Schem1):

K+
-O
HO
1:1(H 2 O :C 2 H 5 O H)
+ 3 K OH
+ 3H 2 O
3
O
potassium Furan-2-carboxylate.
F uran-2-carboxylic ac id .
O
H
K+
H
S
3
O
+M Cl 2
N
H
C H3
N
N H2
1:1(H 2O:C 2H5OH)
HO
N
H
C H3
N
O N H2
O
K2
O
M
O
O
O
O
M= M n(II),Fe(II ),Co( II),N i(II),C u(II),Zn(II) and C d (II )
Figure 1: Scheme (1): Preparation of K2[M(Ceph)(FCA)3] complexes

The formula weights and melting points, are given in(Table I ).Based on the physicochemical
Techscripts

characteristics. All the mixed ligand complexes are colored complexes. They are stable in air at room
temperature, non
hygroscopic and appears as powders with high melting points indicating a strong
metal-ligand bond. The synthesized complexes are sparingly soluble in the common organic solvents
(benzene, chloroform) but they are completely soluble in water, ethanol, acetone and dimethyl form amide
(DMF) solvent.
The complexes were analyzed for their metal by atomic absorption measurements, and chloride
contents were determined by standard methods [11]. Table(1) for all complexes gave approximated values
for theoretical values.The molar conductance values of the metal complexes (measured in 103 M DMF) are
in the range of (93.5-180.5) -1 cm2 mol-1, indicating the electrolytic nature with(2:1).[12]. The atomic
absorption measurements and chloride contents (Table-1) for all complexes gave approximated values for
theoretical values.
B. UV-Visible Spectra and Magnetic Susceptibility Measurements: The values of band positions ( max nm)Cm-1
and molar absorptivity's ( max L cm-1 mol-1) are
listed in Table (2) together with the proposed
assignments transition and magnetic moment values .The electronic spectral studies of mixed ligand
complexes of Mn(II), Fe(II),Co(II), Ni(II),Cu(II), Zn(II), and Cd(II) were carried out in (103 M) DMF solution.
The corrected magnetic moment (eff) in Bohr magneton units of the mixed ligand complexes are given
in Table 2.The electronic spectra of d10[Zn(II) and C d(II)]complexes
do show the charge transfer ,and the
magnetic susceptibility shows that two complexes have diamagnetic moments., because d-d transitions are
not possible hence electronic spectra did not give any fruitful information.in fact this result is a good
agreement with previous work of octahedral geometry.[2,13]. The magnetic moment value for the Ni(II) d8
complex is
3.11 B.M correspond to two unpaired electrons as expected for six coordinated spin free Ni(II)
species suggest an octahedral geometry. [4, 5]

Fe(II)complex exhibits one (d-d) transition electronic spectral band at 26246 cm-1 , which is ascribed to
transitions(5T2g5Eg). Observed value magnetic moment 4.64B.M for Fe (II) complex suggest
distorted
octahedral geometry[12,13].The magnetic moment value for the Co (II) complex is 4.90 B .M. expected for
octahedral geometry [13-14] with high spin paramagnetic d7 system (t2g5eg2) and 3 unpaired electrons.
The magnetic moment values of Mn(II) lie in 5.30 BM indicating octahedral stereochemistry of the
complex [2].The Ni(II) complexes show two(d-d) transition bands
and 26666
cm-1,which
(Table 2) in the region around 21929
are ascribed to transitions 3A2g(F) 3T1g(F) ( 2) and
3A2g(F) 3T1g(P) ( 3), respectively .As the 1 band occurs at low energy, usually in the range not
accessible due to instrumental limitations ,it is not observed in the present cases.
C. FT-IR of Na2 [Mn(Ceph)(FCA)3](1),Na2[Fe(Ceph)(FCA)3](2),Na2[Co(Ceph)(FCA)3](3),Na2[Ni
(Ceph)(FCA)3](4),
Na2[Cu(Ceph)(FCA)3](5),Na2[Zn(Ceph)(FCA)3] (6) and Na2[Cd (Ceph)(FCA)3] (7) complexes: The IR
spectra of the free ligands were compared with those of the metal complexes in order to ascertain the
bonding mode of the drug to metal ion in the complexes. The coordination of metal with the ligands
causes shifts of bands of the ligands to slightly lower or higher frequencies with different intensities [16].
The relevant vibration bands of the free ligand and the complexes are in the region 4004000cm1.The
assignment of the characteristic bands (FT-IR) spectra for the free ligand(Ceph) and (FCAH)
are
summarized in table (3) and (4 ) respectively. The characteristic frequencies of the (1), (2), (3), (4), (5), (6)
and (7) metal complexes are given in Table(5). Interpretation of IR bands of the complex have been carried
out comparing with the spectrum of IR of cephalexin , FCA
and related compound have been well
studied [ 13,17]
The IR spectra of the (FCA) and ( Ceph.) exhibited characteristic band due (C=O) at 1685 cm-1 and
1691 cm-1 [5,18] respectively. The band of (C=O) in the region 1560-1691 cm-1 in the metal complexes
Techscripts

showing the shift
to lower wave numbers confirms that, the carbonyl oxygen is coordinated to the metal
ion [7,10]. IR spectra of the free ligands (FCA)and (Ceph.) exhibited a broad band at 2590 cm-1 along with
shoulder at 3010 cm-1 assignable to (CH) of Phenyl group respectively. A strong band typical of (C=C)
stretching frequency, , are found in 1685 cm-1
in (FCA) and in 1789 cm-1
in ( Ceph) respectively. The
un altered position of a band due to furan ring (C-O-C) and (C-S)in all the metal complexes indicates
that, these groups are not involved in coordination. The new
weak
bands in the region of (501-579) cm-1
and (435-497) cm-1 in the spectra of the complexes are assigned to stretching frequencies of (M-N) and
(M-O) bonds respectively [10,18] which interns support the involvement of oxygen and nitrogen atoms in
coordination [17,19].The asymmetric carboxyl stretching asym(COO) was shifted to higher frequency in
the 1585 and 1589 cm1 range and the symmetric carboxyl stretching sym(COO) was shifted to lower
frequency in the 1379 and 1384 cm1 range, indicating the linkage between the metal ion and carboxylato
oxygen atom. The asymmetric and symmetric stretching vibration of the carboxylate group in the
complexes shows the separation value () greater than 200 cm1.
The large difference () between the asym (-COO ) and sy(-COO) values greater than 200 cm1
indicates the monodentate binding nature of the carboxylato group[17,19]
The results showed that the deprotonated ligand (Furan-2-carboxylic acid (FCA H) to
(Furan-2-carboxylate ion (FCA -) by using (KOH) coordinated to metal ions as a monodendate ligand
through the oxygen atom of the carboxylate group (COO),and the retention of (C-O-C) band of the
(FCA -) ring at 1224 cm-1
oxygen atom of the ring cm-1 indicates that is not taking part in
coordination.[10]
D. Antibacterial Activities studies: The effectiveness of an antimicrobial agent in sensitivity is based on the
zones of inhibition. The synthesized metal complexes were screened for their antimicrobial activity by well
plate method in nutrient agar. The invitro antibacterial activity was carried against 4 hold cultures of
pathogenic bacteria like gram (+)and gram (-) at 37o C. In order to ensure that solvent had no effect on
bacteria, a control test was performed with DMSO and found inactive in culture medium. Antimicrobial
activity was evaluated by measuring the diameter of the inhibition zone (IZ) around the hole. Most of the
tested compounds showed remarkable biological activity against different types of gram positive and
gram negative bacteria. The diameter of the susceptibility zones were measured in mm and the results are
presented in Table (6) Scheme (2). Compounds were considered as active when the (IZ) was greater than 6
mm. The ligand (FCAH) was active against Bacillus only. ( Ceph) and
the all
M(II) complexes showed
antibacterial activity against all the four strains of microbes. The Ni(II) complex was significantly more
active against four strains of microbes and Zn(II) complex shows moderate activity as presented in Table
(6). Scheme (2).A possible explanation is that, in the chelated complex, the positive charge of the metal is
partially shared with the donor atoms in the ligand and there is -electron delocalization over the whole
chelating ring. This, in turn, increases the lipophilic character of the metal chelate and favor's its
permeation through the lipid layers of the membranes of the micro-organism. [20, 21]. Apart from this,
other factors such as solubility, conductivity and dipole moment influenced by the presence of the metal
ions may also be reasons for the increased activity.[ 21,22]
IV. CONCLUSION
In conclusion, the Mn (II),Fe(II) Co(II),Ni(II),Cu(II),Zn(II), and Cd(II) complexes of mixed cephalexin
mono hydrate (antibiotics) and (FCA) are reported. The resultant complexes are characterized by melting
point, conductivity measurement, UV-Vis and Infra-red spectroscopy. Investigation of antimicrobial
activities was carried out against the tested organisms. All the complexes are found to be in octahedral
geometry.
Preliminary
results
indicate
that
newly
synthesized
mixed
ligand
complexes
Na2[M(Ceph)(FCA)3] exhibited promising antibacterial activities and they warrant more consideration as
prospective antimicrobials.
Techscripts


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Techscripts

[21] A Kulkarni, SA Patil,
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Table 1: The physical properties of the compounds
Compounds
Chemical Formula
M . wt
M .p c
Color
(de) c
m
-1
cm2 mol-1
Metal%
Cl%
7.22
1.06
In DMF
Ceph,H = C16H17N3O4S
347.39
off-white
C5H4O3 (FCAH)
112.08
off-white
Na2[Mn(Ceph)(FCA)3]
733.66
light- brown
195de
161.2
7.48 (8.01)
Nil
Na2[Fe(Ceph)(FCA)3]
735.37
Green
113de
95.3
7.59 (7.51)
Nil
Na2[Co(Ceph) (FCA)3]
738.62
red- brown
65de
180.5
7.98 (8.18)
Nil
Na2[Ni( Ceph)(FCA)3]
738.34
Green-deep
236
98.55
7.95 (7.05)
Nil
Na2[Cu( Ceph)(FCA)3]
743.17
Green
115
103.2
8.55 (9.05)
Nil
Na2[Zn(Ceph)(FCA)3]
745.01
light-
255
109.3
8.78 (9.18)
Nil
Na2[Cd(Ceph )(FCA)3]
792.03
Yellow
Yellow
de128
93.5
14.19 (15.28)
Nil
208
132-136de
m = Molar Conductivity,
de =decomposition
Table 2: Electronic Spectral data, magnetic moment, of the mixed ligands complexes
cm-1
max
Compounds
max
Ceph = C16H17N3O4S
279
35842
1503
270
37037
980
* (C=C)
274
36496
20612
780
12820
C5H4O3
(FCA)
Na2[Mn(Ceph)(FCA)3]
280
Na2[Fe(Ceph)(FCA)3]
Na2[Ni(Ceph ) (FCA)3]
Na2[Cu(Ceph )(FCA)3]
345
753
L.mol-1cm-1
Possible assignment
ligand field
6A 1g 4Eg, 4T1g (4P)
35714
2198
28985
15558
13280
eff
BM
5.30
ligand field
CT
5T
2g
4.64
5E2g
286
34965
2308
ligand field
345
28985
1557
CT
607
16474
119
4T1g(F) 4T2g(F)(3)
668
14970
120
4T1g(F)4A2g(F)(2)
273
36630
1463
CT
815
12269
3A2g(F) 3T1g(F)(3)
288
34722
2351
CT
360
27777
1187
CT
4.90
3.11
1.83
Na2[Zn(Ceph )(FCA)3]
272
36764
1411
CT
0.0
285
35087
2229
CT
0.0
Techscripts

Table 3: Data from the infrared Spectrum for the free ligand Ceph (cm-1)
(N-H)
Com.
primary
amine
CephH
3275
(N-H)
Secondary
amide
(C=O)
for
COOH
3219 3049
1759
(C=O)
asm
COO-
-lacta
smy
(C=C)
COO-
arom.
1398
1577
m
1691vs
1595
(C-C
(C-N)
(C-O)
(C-S)
1280
1247
580
alip.
1163
(C-H)
arom.
3010
Table 4: Data from the infrared spectrum for the free ligand Furan-2-carboxylic acid (cm-1)
Compound
OH
(CH)
(C=O)
cyclic
(C-O-C)
(-COO-)
Furan ring
asym
(-COO-)
(-COO-)
sym
sym
FCAH
3142vs
2590
1685
1226 s
1479m
1382m
asym
97
Table 5. Data from the Infrared Spectra M(II)-Mixed ligand complexes of cephalexin mono hydrate and
Furan-2-carboxylic acid(cm-1).
(O-H)
(N-H)
primary
amine
Mn
Fe
Co
Ni
Cu
Zn
Cd
3423
3277
3381s
3140
3392s
3228
3354s
3250
3421s
3248
3435s
3232s
3456s
3211s
(N-H)
Secondary
amide
3045
3045
3064s
3066s
3061s
3057s
3061s
(C=O)
-lactam
& Furan
1691
1566
1583s
1560
1595
1593s
1610s
1560
1608s
1564s
1589s
1560s
(C-O-C)
asm
Furan
COO
smy
COO
ring
(-COO-)
sym-
(C-S)
M-N
582
526w
569
501w
195
584
564w
493w
asym
1229
1228
1226
1591
1396
1454
1355
1583
1365
1477
1371s
1560
1365s
1481s
195
218
M-O
493w
435w
1226
1558s
1367s
119
580
555w
489w
1226
1581s
1361s
220
581
579
472w
1608s
1392
1481
1361s
216
567
536w
472w
582
532w
497w
1226w
1228w
1608
1383
1481
1361s
225
Techscripts

Table 6 . The antibacterial activity (IZ mml) data of M (II)-Mixed Ligand Complexes of
cephalexin mono hydrate and Furan-2-carboxylic acid
Compound
E-coli
Pseudomonas
Staphylococcus
aureus
Bacillus
Control(DMSO)
Furan-2-carboxylic acid
14
ceph
18
16
16
16
Na2[Mn(Ceph)(FCA)3]
16
17
16
15
Na2[Fe(Ceph)(FCA)3]
17
15
17
15
18
16
15
17
Na2[Ni(Ceph ) (FCA)3]
17
17
18
23
Na2[Cu(Ceph )(FCA)3]
19
15
22
18
Na2[Zn(Ceph )(FCA)3]
16
13
15
10
17
16
16
12
Figure 2: Scheme (2): Chart of biological effects of the studied compounds
Techscripts

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Transactions on Engineering and Sciences

Vol.3, Issue 2, February 2015

ISSN: 2347-1964 (Online) 2347-1875 (Print)