Synthesis, Characterization, and Antibacterial Activity of Cd(II) Complexes with 3-/4-Fluorobenzoates and 3-Hydroxypiridine as Co-Ligands

Article abstract of DOI:10.1134/S0036023620090168

Abstract: In this study, two new complexes of Cd(II) 4-fluorobenzoate (4-FB)/3-fluorobenzoate (3-FB) with 3-hydroxypyridine (3-HPY) have been synthesized and structural characterizations have been performed by using elemental analysis, FT-IR spectroscopy,

Full text of DOI:10.1134/S0036023620090168

ISSN 0036-0236, Russian Journal of Inorganic Chemistry, 2020, Vol. 65, No. 9, pp. 1351–1359. © Pleiades Publishing, Ltd., 2020.
COORDINATION
COMPOUNDS
Synthesis, Characterization, and Antibacterial Activity
of Cd(II) Complexes with 3-/4-Fluorobenzoates
and 3-Hydroxypiridine as Co-Ligands
Mustafa Sertçelika, * and Murat Durmanb
aKafkas University, Department of Chemical Engineering, Faculty of Engineering and Architecture, Kars, 36100 Turkey
bKafkas University, Institute of Science, Kars, 36100 Turkey
*e-mail: mustafasertcelik@gmail.com
Received January 13, 2020; revised February 10, 2020; accepted March 3, 2020
Abstract—In this study, two new complexes of Cd(II) 4-fluorobenzoate (4-FB)/3-fluorobenzoate (3-FB)
with 3-hydroxypyridine (3-HPY) have been synthesized and structural characterizations have been per-
formed by using elemental analysis, FT-IR spectroscopy, and single-crystal X-ray diffraction methods. In
both complexes, the metal atom is chelated by two carboxylate groups from two 4- or 3-fluorobenzoate anions
and coordinated by two 3-hydroxypyridine (HPY) molecules. In both complexes, an oxygen atom of carbox-
ylate from the adjacent anion bridges to the Cd atom, completing the distorted seven-coordination geometry.
The only difference between complexes is the positions of fluorine atoms in fluorobenzoic acids (4-fluoro-
benzoic acid (complex 1) and 3-fluorobenzoic acid (complex 2)). Antibacterial resistance of two new com-
plexes to some bacteria has been investigated.
Keywords: cadmium(II) complex, 4-fluorobenzoic acid, 3-fluorobenzoic acid, 3-hydroxypyridine, antibac-
terial, X-ray diffraction
DOI: 10.1134/S0036023620090168
INTRODUCTION
important role in many biological systems, as compo-
nents of various vitamins and drugs [13–15].
In recent years, the synthesis of new complexes
with striking properties that can be used in various
application areas has gained importance. These com-
plexes are composed of metal atom/atoms at the cen-
ter of symmetry and anions or molecules attached to
the metal atom. These complexes stand out both with
the variety of their structure and with their physical,
chemical and biological properties. The structure and
application-oriented properties of these compounds,
which are part of material chemistry, are influenced by
metal cations, ligands, and intra- and intermolecular
interactions [1–7].
Antibiotics are the basic life-saving drugs that rev-
olutionized the pharmaceutical world with the discov-
ery of penicillin in 1928. Recently, bacterial infections
have caused deadly diseases and widespread outbreaks
in humans, increasing at an alarming rate. As a result
of the erroneous and widespread use of antibiotics, the
antibiotic resistance, which is defined as the ability of
microorganisms to resist the effects of drugs, emerges.
It has also been noted that there are mortal cases due
to infection from antibiotic-resistant bacteria. When
this situation is evaluated, the choice of the most
appropriate antibiotic against infection is of vital
importance. The increase in mortality associated with
infectious diseases is directly related to bacteria that
are resistant to antibiotics. The development of new
antimicrobial agents with new and stronger mecha-
nisms of action is certainly an urgent medical need
[16–23].
Carboxylic acids and ligands containing N-, O-,
and S-donor atoms in their structure have many bio-
logical activities such as anti-inflammatory, antibacte-
rial, antitumor, and antifungal [8–11]. Recent studies
on antimicrobial activity of non-steroidal anti-inflam-
matory drugs have shown the increased antimicrobial
activity of transition metals complexes with various
carboxylic acid and nitrogen-containing ligands [12].
Therefore, it is very important to learn about the
In this study, two new complexes of Cd(II) 4-/3-
fluorobenzoates with 3-hydroxypyridine, [Cd2(4-
FB)4(3-HPY)4] (1) and [Cd2(3-FB)4(3-HPY)4] (2),
structure and binding relationships of complexes in were firstly synthesized and their structures were char-
the preparation of effective antimicrobial species [12]. acterized by elemental analysis, FT-IR spectroscopy
Heterocyclic compounds are known to play an and single crystal X-ray diffraction methods and anti-
1351

1352
MUSTAFA SERTÇELIK, MURAT DURMAN
Table 1. Crystal and structure refinement data of complexes 1 and 2
Crystal data
Chemical formula
Complex 1
Complex 2
C48H36Cd2F4N4O12
C48H36Cd2F4N4O12
FW
1161.61
Triclinic, P
1161.61
Triclinic, P
Crystal system, space group
Temperature, K
a, b, c, Å
296
296
8.7635 (3), 11.8088 (4), 12.1645 (4)
93.866 (2), 110.079 (2), 98.280 (2)
1160.74 (7)
10.2492 (2), 10.2769 (2), 12.0497 (3)
66.183 (2), 86.824 (3), 87.985 (3)
1159.21 (4)
α, β, γ, deg
V, Å3
Z
1
1
Radiation type
μ, mm−1
MoKα
1.00
MoKα
1.00
Crystal size, mm
Data collection
Diffractometer
Absorption correction
Tmin, Tmax
0.17 × 0.12 × 0.09
0.12 × 0.10 × 0.09
Bruker APEX-II CCD
Multi-scan SADABS; Bruker, 2012
0.568, 0.745
Bruker APEX-II CCD
Multi-scan SADABS; Bruker, 2012
0.879, 0.905
No. of measured, independent and
17479, 4694, 4279
14282, 4582, 3795
observed [I > 2σ(I)] reflections
Rint
0.034
0.626
0.053
0.627
(sinθ/λ)max (Å−1)
Refinement
R[F2 > 2σ(F2)], wR(F2), S
0.029, 0.060, 1.16
0.085, 0.184, 1.39
No. of reflections
4694
317
4582
316
No. of parameters
H-atom treatment
H-atom parameters constrained H atoms treated by a mixture of independent and
constrained refinement
2
w = 1/[σ2( ) + (0.P)2 + 11.2792P]
Fo
2
where P = ( + 2 2)/3
Fo
Fc
Δρmax, Δρmin (e Å−3)
0.41, −0.42
1.49, −0.83
Computer programs: APEX2 [43], SAINT [43], SAINT, SHELXS97 [44], SHELXL97 [44], ORTEP-3 for Windows [45], WinGX pub-
lication routines [45] and PLATON [46].
bacterial properties of the obtained complexes were any purification. Elemental Analysis was measured
investigated by agar well diffusion method against
Pseudomonas aeruginosa (P. aeruginosa), Klebsiella
pneumonia (K. pneumonia), Escherichia coli (E. coli),
and Staphylococcus aureus (S. aureus) bacteria.
with LECO CHNS-932 elemental analyzer. FT-IR
Spectra were recorded by a PerkinElmer FrontierTM
FT-IR spectrometer using a Diamond ATR accessory
in the range of 4000–600 cm–1 from solid samples.
Crystal structures were determined by Bruker SMART
BREEZE CCD diffractometer. The experimental
details related to the crystal structures of complexes
were given in Table 1.
EXPERIMENTAL
Materials and methods. Chemicals used in the
study; 4-fluorobenzoic acid, 3-fluorobenzoic acid
(Fluka), 3-hydroxypyridine (Merck), sodium bicar-
bonate (Merck) and cadmium(II) sulfate 8.3 hydrate
CdSO4 ⋅ 8.3H2O (Merck) were taken and used without
Synthesis of the complexes. Bis(μ-4-fluorobenzo-
3
3
2
ato)-κ O,O':O;κ O:O,O'-bis[(4-fluorobenzoato-κ O,O')
bis(3-hydroxypyridine-κN1)cadmium] (complex 1). To
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY
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SYNTHESIS, CHARACTERIZATION, AND ANTIBACTERIAL ACTIVITY
obtain the sodium 4-fluorobenzoate, 0.84 g (0.01 mol) RESULTS AND DISCUSSION
1353
of 4-fluorobenzoic acid and 1.40 g (0.01 mol) of
sodium bicarbonate were mixed in 100 mL distilled
water and continuously heated and stirred at 60°C
until CO2 gas was removed. Then 3.84 g (0.005 mol) of
CdSO4 ⋅ 8.3H2O dissolved in 50 mL of distilled water.
In a separate beaker, 1.75 g (0.01 mol) of 3-hydroxy-
pyridine solution was prepared and added on cad-
mium sulfate solution, and the sodium salt of 4-fluo-
robenzoic acid was added by filtration, then left to
crystallize. After 5–6 days, cream colored crystals
formed. For complex 1, anal. calcd. (%): [Cd2(4-
FB)4(3-HPy)4] (MW = 1161.61) C, 49.46; H, 3.46; N,
4.81. Found (%): C, 49.6; H, 3.12; N, 4.82. Selected
Elemental analysis, FT-IR spectroscopy, and
X-ray structure analysis results are in harmony for the
two new complexes synthesized.
FT-IR spectroscopy. Some important stretching
bands of FT-IR spectra of synthesized complexes are
as follows. The peaks of the O–H group of the com-
plexes were recorded in the range of 3600–3300 cm–1.
The O–H stretching vibrations of the complexes were
observed at 3290 cm–1 (1), 3149 cm–1 (2) [29]. The
carbonyl group COO– asymmetric and symmetric
vibrations were observed at 1540–1392 cm–1 (1),
1537–1386 cm–1 (2) The vibrations related to the Me-
O bond were recorded at 641 cm–1 (1) and 640 cm–1
(2) [29, 30]. The C–N absorption bands of pyridine
ring were showed at 1089 cm–1 (1) and 1050 cm–1 (2)
[31] (Figs. S1 and S2).
IR bands (cm−1):
3290, ν(C–N)py, 1089,
ν(OH)H O
2
νCOO–)as 1540, ν(COO–)s 1392, ν(C=C)ar 1600,
ν(M–O) 641 cm–1.
Descriptions of the crystal structures. The metal
atoms are chelated by four oxygen atoms of two car-
boxylate groups from two 4-fluorobenzoate anions
(for complex 1) and two 3-fluorobenzoate anions (for
complex 2), and coordinated by two 3-hydroxypyri-
dine molecule; In both complexes, an O atom of car-
3
3
Bis(μ-3-fluorobenzoato)-κ O,O':O;κ O:O,O'-
2
bis[(3-fluorobenzoato-κ O,O') bis(3-hydroxypyridine-
κN1)cadmium] (complex 2). The synthesis of complex
1 was repeated using 3-fluorobenzoic acid instead of
4-fluorobenzoic acid. After 5–6 days, cream colored
crystals formed. For complex 2, anal. calcd. (%): boxylate from the neighboring anion bridges to the Cd
[Cd2(3-FB)4(3-HPy)4] (MW = 1161.61) C, 49.46; H,
3.46; N, 4.81. Found (%): C, 49.20; H, 3.12; N, 4.82;
atom, creating the uneven seven-coordination envi-
ronment (Figs. 1 and 2). The Cd(1)–Cd(1)i (Symme-
try code: (i) –x, –y, –z) distances are 3.812(8) Å (1)
and 3.838(8) Å (2). Bond length of the average Cd–O
(Table 2) is 2.4064(19) Å (complex 1) and 2.431(6) Å
(2). The Cd atom is displaced out of the least-squares
planes of the carboxylate groups (O(1)/C(1)/O(2))
and (O(3)/C(8)/O(4)) by 0.0124(2) and 0.0627(2) Å
(1) and 0.0433(7) and –0.0327(7) Å (2), respectively.
The OCdO angles are 52.78(6)°and 53.81(6)°(for 1) and
53.5(2)°and 52.0(2)°(for 2), respectively. In the previous
researches, the OMO (where M is transition metal)
angles were found 55.71(5)° and 117.52(4)° in [Cd2(4-
methylaminobenzoate)4(nicotinamide)2(H2O)2] [32],
55.96(4)° and 53.78(4)° in [Cd2(4-dimethylamino-
benzoate)4(nicotinamide)2(H2O)2] [33], 52.91(4)°
and 53.96(4)° in [Cd(4-formylbenzoate)2(isonicotin-
amide)2(H2O)] · H2O [34], 60.70(4)° in [Co(4-dime-
thylaminobenzoate)2(isonicotinamide)(H2O)2] [35],
58.45(9)° in [Mn(4-dimethylaminobenzoate)2(ison-
icotinamide)(H2O)2] [36], 60.03(6)° in [Zn(4-
methylaminobenzoate)2(isonicotinamide)2] ⋅ H2O
[37], 58.3(3)° in [Zn2(N,N-diethylnicotinamide)2(4-
hydroxybenzoate)4] ⋅ 2H2O [38] and 55.2(1)° in
[Cu(acetylsalicylate)2(pyridine)2] [39]. The dihedral
angles between the planar carboxylate groups
(O(1)/O(2)/C(1)), (O(3)/O(4)/C(8)) and the neigh-
boring benzene rings A (C(2)–C(7)), B (C(9)–C(14))
are 1.5(2)° and 3.8(2)° (1) and 3.5(3)° and 1.5(8)° (2),
respectively, while that between rings A and B is A/B =
11.8(1)° (1) and 3.7(4)° (2). The pyridine rings of 3-
HPY C (N(1)/C(15)–C(19)) and D (N(2)/C(20)—C(24))
Selected IR bands (cm−1):
3149 ν(C–N)py.
ν(OH)H O
2
1050, νCOO–)as 1537, ν(COO–)s 1386, ν(C=C)ar 1601,
ν(M–O) 640 cm–1.
Determination of antimicrobial activity of com-
plexes. Antibacterial effects of complexes were investi-
gated using agar well diffusion method. The bacteria
used were Gram-negative P. aeruginosa (ATCC
27853), K. pneumoniae (ATCC 4352), and E. coli
(ATCC 25922), Gram-positive S. aureus (ATCC)
6538). Microorganisms obtained from company of
Microbiological Environmental Protection Laborato-
ries were grown in research laboratories of Kafkas
University Engineering and Architecture Faculty.
Mueller Hinton Agar (MHA) was used as medium.
First, the activation of bacteria from stocks in Mueller
Hinton Broth (MHB) was performed for 24 hours
during the 37°C incubation. Bacteria which were stan-
dardized with 0.5 McFarland standard were planted in
sterile prepared petri dishes. 0.05 g of the synthesized
complexes and standard antibiotics (Ampicillin
X3261, Neomycin X3385, Steptomycin X3385) were
dissolved in 5 mL of DMSO and homogeneous solu-
tions were prepared and injected 50 μL from the stocks
into wells drilled 4 mm in diameter using an auto-
mated pipette. Petri dishes were at for incubated at
37 1°C for (18–24) 2 hours in order to determine
inhibition zone diameters [24–28]. All inhibition
zones were measured as mm.
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MUSTAFA SERTÇELIK, MURAT DURMAN
F(2)
C(17)
C(13)
O(5)
C(16)
C(18)
C(14)
C(9)
C(12)
C(11)
C(19)
C(15)
O(3)
C(8)
N(1)
C(10)
O(4)
O(1)
Cd(1)
C(1)
C(3)
C(2)
C(4)
C(5)
O(2)
F(1)
N(2)
C(20)
C(7)
C(24)
C(23)
C(6)
C(21)
O(6)
C(22)
Fig. 1. The molecular structure of the dinuclear complex 1 with the atom numbering scheme. Thermal ellipsoids are created at
the 30% probability level. Hydrogen atoms have been removed for clarity.
O(6)
F(1)
C(22)
C(5)
C(21)
C(20)
C(4)
C(3)
C(6)
C(7)
C(23)
C(2)
O(2)
N(2)
C(1)
O(1)
C(24)
Cd(1)
O(4)
C(8)
C(15)
N(1)
O(5)
O(3)
C(10)
C(9)
C(16)
C(17)
C(19)
C(18)
C(11)
C(12)
C(14)
F(2)
C(13)
Fig. 2. The molecular structure of the dinuclear complex 2 with the atom numbering scheme. Thermal ellipsoids are created at
the 30% probability level. Hydrogen atoms have been removed for clarity.
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SYNTHESIS, CHARACTERIZATION, AND ANTIBACTERIAL ACTIVITY
Table 2. Selected bond lengths (Å) and angles (°) for complexes
Complex 1
1355
Complex 2
Bond lengths
Cd(1)–O(1)
2.3027(18)
2.3254(18)
2.327(2)
2.328(2)
2.3625(19)
2.461(2)
Cd(1)–N(2)
Cd(1)–N(1)
2.313(7)
2.316(7)
2.323(6)
2.350(6)
2.362(6)
2.483(6)
2.637(6)
1.241(10)
1.288(10)
1.241(10)
1.276(11)
Cd(1)–O(2)i
Cd(1)–N(2)
Cd(1)–N(1)
Cd(1)–O(4)
Cd(1)–O(3)
Cd(1)–O(1)
Cd(1)–O(2)i
Cd(1)–O(2)
Cd(1)–O(4)
O(1)–C(1)
O(2)–C(1)
O(3)–C8
Cd(1)–O(3)
Cd(1)–O(2)
O(1)–C(1)
O(2)–C(1)
O(3)–C(8)
O(4)–C(8)
2.5802(19)
1.251(3)
1.257(3)
1.258(3)
1.254(3)
O(4)–C8
Bond angles
O(1)Cd(1)O(2)i
O(1)Cd(1)N(2)
N(2)Cd(1)N(1)
130.85(7)
92.49(7)
87.04(7)
93.36(7)
87.42(7)
173.73(7)
138.45(7)
90.55(7)
177.0(3)
N(2)Cd(1)O(3)
N(1)Cd(1)O(3)
89.5(2)
87.5(2)
90.9(2)
91.4(2)
136.2(2)
90.5(2)
89.5(2)
O(2)iCd(1)N(2)
O(1)Cd(1)N(1)
N(2)Cd(1)O(1)
N(1)Cd(1)O(1)
O(2)iCd(1)N(1)
N(2)Cd(1)N(1)
O(1)Cd(1)O(4)
O(3)Cd(1)O(1)
N(2)Cd(1)O(2)i
N(1)Cd(1)O(2)i
O(2)iCd(1)O(4)
N(2)Cd(1)O(4)
O(3)Cd(1)O(2)i
N(2)Cd(1)O(2)
N(1)Cd(1)O(2)
O(1)Cd(1)O(2)
85.36(7)
91.76(7)
85.32(6)
143.67(6)
95.74(7)
87.01(7)
53.81(6)
52.78(6)
87.36(7)
94.37(7)
166.84(6)
138.10(6)
95.0(2)
91.3(2)
91.6(2)
53.5(2)
88.2(2)
90.1(2)
52.0(2)
119.0(7)
121.0(8)
N(1)Cd(1)O(4)
O(1)Cd(1)O(3)
O(2)iCd(1)O(3)
N(2)Cd(1)O(3)
N(1)Cd(1)O(3)
O(4)Cd(1)O(3)
O(1)Cd(1)O(2)
N(2)Cd(1)O(2)
N(1)Cd(1)O(2)
O(4)Cd(1)O(2)
O(3)Cd(1)O(2)
N(2)Cd(1)O(4)
N(1)Cd(1)O(4)
O(3)Cd(1)O(4)
O(1)C(1)O(2)
O(3)C(8)O(4)
Symmetry code: (i) –x + 1, −y + 1, −z + 1.
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 65 No. 9 2020

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MUSTAFA SERTÇELIK, MURAT DURMAN
Table 3. Hydrogen-bond geometry (Å, deg)
D–H···A
D—H
H···A
D···A
D—H···A
Complex 1
O(5)–H(5)···O(6)ii
O(6)–H(6)···O(3)iii
C(7)–H(7)···O(4)i
C(3)–H(3)···Cg(4)iv
0.82
0.82
0.93
0.93
1.92
2.727(3)
2.577(3)
3.314(5)
3.888(3)
168
163
172
172
1.78
2.39
2.96
Complex 2
O(5)–H(5)A···O(4)ii
O(6)–H(6)A···O(4)iii
C(3)–H(3)···O(3)i
C(6)–H(6)···F(2)iv
0.82
0.82
0.93
0.93
2.00
2.715(10)
2.720(11)
3.265(12)
3.224(18)
146
147
171
131
2.00
2.34
2.54
Symmetry codes (1): (i) –x + 1, −y + 1, −z + 1; (ii) x + 1, y + 1, z; (iii) −x, −y + 1, −z + 1; (iv) −x + 2, −y + 1, −z + 1. Cg4
is the centroid or ring D (N2/C20—C24).
Symmetry codes (2): (i) −x + 1, −y + 1, −z + 1; (ii) −x + 2, −y + 1, −z + 1; (iii) −x + 1, −y, −z + 1; (iv) −x + 2, −y, −z + 1.
are positioned at a dihedral angle of C/D = 3.2(1)° B/D = 85.4(1)° (1) and A/C = 88.9(3)°, A/D =
(Complex 1) and 13.0(3)° (2), while they are oriented 80.1(2)°, B/C = 87.1(3)° and B/D = 81.5(3)° (2). In
the crystal structure, the bifurcated O–H…O hydrogen
bonds (Table 3) connect the molecules, via the
with respect to the benzene rings at dihedral angles of
A/C = 83.6(1)°, A/D = 83.8(1)°, B/C = 85.8(1)° and
Fig. 3. A partial packing diagram of complex 1. Only the O–H···O hydrogen bonds are shown as dashed lines.
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SYNTHESIS, CHARACTERIZATION, AND ANTIBACTERIAL ACTIVITY
1357
c
0
b
a
Fig. 4. A partial packing diagram viewed down the c-axis of complex 2. Only the bifurcated O–H···O hydrogen bonds are shown
as dashed lines. Remaining hydrogen atoms have been removed for clarity.
R22(14) and R22(24) (1) and R22(14) and R22(28) could be instrumental in the stabilization of the struc-
(2) ring motifs [40], into a network (Figs. 3 and 4), ture. For complex 1, a weak C–H-π interaction (Table
they are then connected by the C–H—O hydrogen 3) was also observed. For complex 2, the π–π contacts
bonds (Table 3) into a 3D structure, in which they between the pyridine rings, Cg3–Cg3i and Cg4–
Table 4. Antibacterial zone diameters of complexes (mm)
Complex
P. aeruginosa
K. pneumoniae
E. coli
S. aureus
Complex 1
Complex 2
Ampicillin X3261
Neomycin X3385
Steptomycin X3385
30
30
36
17
12
26
30
35
16
11
28
26
34
16
10
31
30
37
13
21
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MUSTAFA SERTÇELIK, MURAT DURMAN
CCDC nos. 1952575 (1) and 1952576 (2). Copies of these
data can be obtained free of charge on application to
CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax:
Cg4ii, and benzene rings, Cg2–Cg2iii [symmetry
codes: (i) 2 – x, 1 – y, 1 – z, (ii) 1 – x, –y, 1 – z, (iii)
2 – x, –y, 2 – z, where Cg2, Cg3 and Cg4 are the cen-
troids of the rings B (C(9)–C(14)), C (N(1)/C(15)–
C(19)) and D (N(2)/C(20)–C(24)), respectively]. It
was suggested that the structure could be stabilized,
along with centroid–centroid distances of 3.904(6),
3.725(6), and 3.742(7) Å, respectively.
Antimicrobial activity of complexes. The antimicro-
bial effects of complex 1 and complex 2 were examined
and zone diameters are given in Table 4. When we look
at the zone diameters, both complexes are effective
[41, 42] against P. aeruginosa, K. pneumoniae, E. coli
and S. aureus bacteria and Ampicillin X3261, Neomy-
cin X3385, Steptomycin X3385 as standart.
(+44)
1223
336033,
or
online
by
via www.ccdc.cam.ac.uk/data_request/cif,
emailing data_request@ccdc.cam.ac.uk.
or
Supporting information includes FT-IR (Figs. S1, S2),
and cif data (Figs. S3, S4) for compounds 1 and 2 synthe-
sized in this work.
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