Synthesis, characterization, and antibacterial activity of two zinc(II) complexes with Schiff bases derived from rimantadine

Article abstract of DOI:10.1134/S1070328414050054

The reactions of zinc(II) chloride and two Schiff base ligands derived from rimantadine and 5-chlorosalicylaldehyde/4-methoxysalicylaldehydes, generated two novel complexes [Zn(L¹)₂Cl₂] (I) and [Zn(L²)₂Cl₂] (II), where L¹ = 2-((1-(1-adamantan-1-yl)ethyl)-iminomethyl)-4-chlorophenol, L² = 2-((1-(1-adamantan-1-yl)ethyl)iminomethyl)-5-methoxyphenol. The complexes were characterized by the means of IR, ¹H NMR, elemental analysis, molar conductance and thermal analysis. A single-crystal X-ray diffraction analysis reveals that both complexes crystallize in orthorhombic system, space group Fdd2 for I and Pbcn for II. In two complexes crystals, each asymmetric unit consists of one zinc(II) ion, two corresponding Schiff base ligands and two chlorine atoms; the central zinc atom lies on a twofold rotation axis and is four-coordinate via two chlorine atoms and two oxygen atoms from the Schiff base ligands, forming a distorted tetrahedral geometry.

Full text of DOI:10.1134/S1070328414050054

ISSN 1070ꢀ3284, Russian Journal of Coordination Chemistry, 2014, Vol. 40, No. 6, pp. 371–378. © Pleiades Publishing, Ltd., 2014.
Synthesis, Characterization, and Antibacterial Activity
of Two Zinc(II) Complexes with Schiff Bases Derived
from Rimantadine1
X. D. Jina, *, C. Xua, X. Y. Yina, H. B. Wanga, Z. Y. Zoub, D. L. Liua, C. H. Gea,
X. H. Changa, and Y. H. Jinc
a College of Chemistry, Liaoning University, Shenyang, 110036 P.R. China
b Department of Life Science, Liaoning University, Shenyang, 110036 P.R. China
c Liaoning Provincial Institute of Measurement, Shenyang, 110036 P.R. China
*eꢀmail: jinxudong@yahoo.com
Received September 6, 2013
Abstract
—
The reactions of zinc(II) chloride and two Schiff base ligands derived from rimantadine and 5ꢀchloꢀ
rosalicylaldehyde/4ꢀmethoxysalicylaldehydes, generated two novel complexes [Zn(L1)2Cl2]
(I)
and
[Zn(L2)2Cl2] (II), where L1 = 2ꢀ((1ꢀ(1ꢀadamantanꢀ1ꢀyl)ethyl)ꢀiminomethyl)ꢀ4ꢀchlorophenol, L2 = 2ꢀ((1ꢀ
(1ꢀadamantanꢀ1ꢀyl)ethyl)iminomethyl)ꢀ5ꢀmethoxyphenol. The complexes were characterized by the means
of IR, 1H NMR, elemental analysis, molar conductance and thermal analysis. A singleꢀcrystal Xꢀray diffracꢀ
tion analysis reveals that both complexes crystallize in orthorhombic system, space group Fdd2 for I and Pbcn
for II. In two complexes crystals, each asymmetric unit consists of one zinc(II) ion, two corresponding Schiff
base ligands and two chlorine atoms; the central zinc atom lies on a twofold rotation axis and is fourꢀcoordiꢀ
nate via two chlorine atoms and two oxygen atoms from the Schiff base ligands, forming a distorted tetraheꢀ
dral geometry.
DOI: 10.1134/S1070328414050054
1
INTRODUCTION
for its taking part in a particular metabolic process [13,
14]. The Zn(II) complexes with Schiff bases were also
found to be with biological activity and they demonꢀ
strated enhanced activities as compared to their paꢀ
rental ligands [15, 16]. In view of these points above,
we designed and managed to synthesize a series of
complexes containing both metal zinc(II) ion and the
ligands derived from rimantadine and substituted saliꢀ
cylaldehyde. We hoped these zinc complexes could exꢀ
hibit an extraordinary biological activity. In this work,
The field of Schiff base complexes attracts interest
mainly due to facile synthesis and biological activity
[1–4]. The diverse structures for the ligands rest with
the types of aldehydes and amines [5]. Although obꢀ
tained ligands involve in a broad scope such as single,
double, asymmetric and macrocyclic Schiff bases,
etc., the biological activity study of rimantadineꢀsaliꢀ
cylaldehyde (or substituted salicylaldehyde) Schiff
bases and their corresponding complexes has not been
reported in detail [6].
two fourꢀcoordinate zinc(II) complexes [Zn(L1)2Cl2] (
I)
and [Zn(L2)2Cl2] (II), where L1 = 2ꢀ((1ꢀ(1ꢀadamantanꢀ
1ꢀyl)ethyl)ꢀiminomethyl)ꢀ4ꢀchlorophenol, L2 = 2ꢀ((1ꢀ
(1ꢀadamantanꢀ1ꢀyl)ethyl)iminomethyl)ꢀ5ꢀmeꢀthoxyꢀ
phenol, were reported. Their absolute structures were
determined by a singleꢀcrystal Xꢀray diffraction analyꢀ
sis. The antibacterial activities of two Schiff
base ligands and their complexes against two bacteria
of Escherichia coli and Bacillus subtilis were synchroꢀ
nously investigated.
The clinic medical research indicated that both
amantadine (SymmetrelTM) and rimantadine (Fluꢀ
madineTM) could block the ion channel formed by the
M2 protein of influenza A viruses, result in inhibiting
the early stages of virus replication. Therefore in many
countries, amantadine and rimantadine have been
widely used to treat or prevent seasonal influenza as efꢀ
ficacious remedies [7–10]. However, the incidence of
side effects to centralꢀnervousꢀsystem was higher with
amantadine [11]. Salicylaldehyde and its derivatives
are with antibacterial and antiviral activity and they
were used to produce efficient herbicides, insecticides
and fungicides [12]. Zinc is a vital element in the life
EXPERIMENTAL
Materials and methods. All chemicals and solvents
were of analytical grade and used as received. Elemental
analysis was carried out on PerkinElmer Flash EA 1112.
1
The article is published in the original.
371

372
JIN et al.
Chemical shifts (
300 MHz on a Varian MercuryꢀVx300 spectrometer in
CDCl3 solvent containing TMS as an internal standard.
δ
) for 1H NMR spectra were recorded at complexes in DMF (1.0 10–3 mol L–1) was measured
×
on a DDSꢀ11A conductormeter.
Synthesis of ligands. Two Schiff base ligands, 2ꢀ((1ꢀ(1ꢀ
Infrared spectrum (IR) was scanned in the range 4000 to adamantanꢀ1ꢀyl)ethyl)ꢀiminoꢀmethyl)ꢀ4ꢀchlorophenol
1) and 2ꢀ((1ꢀ(1ꢀadamantanꢀ1ꢀyl)ethyl)iminomethꢀ
yl)ꢀ5ꢀmethoxyphenol (
2), were prepared analogously
to the literatures [17–20]. The synthetic route in this
400 cm–1 with KBr pellets on a Nicolet NEXUS FTꢀ
IR 5700 spectrophotometer. Melting points were meaꢀ
sured on a WRSꢀ1B micro melting point apparatus
(L
L
which were uncorrected. The molar conductance of the work was shown below:
OHC
R
R
KOH
C H OH
HO
C H OH
2
N
2
5
5
NH2⋅ HCl
NH2
H
O
L1: R = 4ꢀCl; L2: R = 5ꢀOCH3
Rimantadine hydrochloride (3.0 mmol) and KOH corrected the intensities for Lorentz and polarization
(3.0 mmol) in 50 mL anhydrous alcohol were stirred effect [18]. An empirical absorption correction was
for 24 h. The produced white precipitates (KCl) were applied using the SADABS program [19]. The strucꢀ
filtered out and the transparent liquid was added dropꢀ tures were solved by direct methods using the program
wise to aldehyde (3.0 mmol) in 30 mL anhydrous alcoꢀ SHELXSꢀ97 and all nonꢀhydrogen atoms were refined
anisotropically on F2 by the fullꢀmatrix leastꢀsquares
technique using the SHELXLꢀ97 crystallographic
software package [20]. The hydrogen atoms were genꢀ
erated geometrically. All calculations were performed
on a personal computer with the SHELXLꢀ97 crystalꢀ
lographic software package. The details of the crystal
parameters, data collection and refinement are sumꢀ
marized in Table 1. Selected bond lengths and angles
with their estimated standard deviations are given in
Table 2. The molecular structures, as shown in Fig. 1,
were visualized by Diamond [21].
hol under constant stirring. The resulting solution was
refluxed for ~4 h, concentrated to about 20 mL through
reduced pressure distillation and then stood at room
temperature. A yellow solid appeared after 2–3 days
with the solvent evaporation. The solid was filtered off
and washed with anhydrous alcohol three times and
airꢀdried.
Syntheses of the complexes. Zinc(II) chloride
(1.0 mmol) in 20 mL anhydrous alcohol was added
dropwise to a hot solution of a Schiff base ligand
(1.0 mmol) in 20 mL anhydrous alcohol. Thereafter
the mixture was refluxed for about 2 h and then kept at
room temperature for overnight and complex precipiꢀ
tates were filtered off and dried. The yields were 58%
Supplementary material for complexes
has been deposited with the Cambridge Crystalloꢀ
graphic Data Centre (nos. 886789 ( ), 853684 (II);
I and II
I
for I and 62% for II.
deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk).
For C38H48N2O2Cl4Zn (
anal. calcd., %: C, 59.12;
Found, %: C, 58.97;
I
) (
M
= 771.99)
H, 6.27;
H, 6.16;
RESULTS AND DISCUSSION
N, 3.63.
N, 3.51.
The main IR data for I and II are given in Table 3,
wherein several main data for ligands are also provided
for comparison. Broad and intensity absorptions at
3433–3449 cm–1 for ligands and complexes can be
For C40H54N2O4Cl2Zn (II) (
M
= 763.15)
H, 7.13;
H, 6.89;
anal. calcd., %: C, 62.95;
N, 3.67.
N, 3.63.
identified as ν(O–H) indicating that phenolic hydroxꢀ
Found, %:
C, 62.70;
yls of ligands are not deprotonated when the complexꢀ
es are formed. The strongest absorptions at 1632 and
1623 cm–1 for ligands as well as 1648 and 1643 cm–1 for
The molar conductance values (ΛM) are 6.10 and
8.64 S cm2 mol–1 for
and II, respectively, which beꢀ
I
the complexes are the characteristics of ν(C=N); in
metal complexes these bands undergo upward shift by
15 and 20 cm–1. The spectra of the ligands show strong
bands at 1279 cm–1 for L1 and 1221 cm–1 for L2, which
long to the complex type of nonꢀelectrolytes molecuꢀ
lar [17].
Xꢀray structure determination. Suitable crystals
I and II were grown by slow solvent evaporation of
is fairly certain to
bration band occurs at slight lower frequency with
a Bruker Smart Apex II CCD with graphite monoꢀ 1235 cm–1 for
and with 1214 cm–1 for II. The absorpꢀ
chromated MoKα radiation ( = 0.71073 ) at
ν(C–O). In the complexes, this viꢀ
of
anhydrous alcohol. Diffraction data were collected on
I
tions at 483 and 496 cm–1 for
and II are attributed to
I
λ
Å
298(2) K using the ωꢀscan technique. The data were (Zn–O), indicating that oxygens of the Schiff bases
integrated by using the SAINT program, which also are coordinated to Zn.
ν
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SYNTHESIS, CHARACTERIZATION, AND ANTIBACTERIAL ACTIVITY
373
Table 1. Crystal data and structure refinement information for compounds
I
and II
Value
Parameter
I
II
Formula weight
Crystal system
Space group
771.59
Orthorhombic
Fdd2
763.12
Orthorhombic
Pbcn
a
, Å
, Å
15.5281(12)
43.024(15)
10.9346(13)
7305(3)
8
13.2436(14)
12.3110(13)
24.888(2)
4057.8(7)
4
b
c
, Å
Volume, Å3
Z
ρcalcd, mg/m3
1.403
1.249
Absorption coefficient, mm–1
1.001
0.777
F
(000)
Crystal size, mm
Range for data collection, deg
3232
1616
0.40
×
0.30
×
0.20
0.40
× 0.37 × 0.24
θ
2.37–23.08
3.35–23.12
Limiting indices
–18
–50
≤
≤
h
k
≤
≤
≤
15,
49,
12
–15
–14
≤
≤
h
k
≤
≤
≤
14,
11,
29
–12
≤
l
–29 ≤ l
Reflections collected
7027
19265
Independent reflections (Rint
Data/restraints/parameters
Goodnessꢀofꢀfit on F 2
)
3096 (0.0269)
3096/1/199
3584 (0.0497)
3584/0/224
1.070
1.020
Final
R
indices (
I
> 2σ(I
))*
R
1 = 0.0405, wR2 = 0.0839
1 = 0.0490, wR2 = 0.0897
R
1 = 0.0505, wR2 = 0.01190
R
indices (all data)*
R
R1 = 0.0930, wR2 = 0.1491
Absorption correction
Empirical
Fullꢀmatrix leastꢀsquares on F 2
0.24/–0.19 0.49/–0.19
Refinement method
Δρmax/Δρmin, e
Å–3
*
R
= S||F
| – |
F
||/|
F
|; wR = [S
w
(Fo2
–
Fc2)2 Σw(Fo2)2]1 2
.
1
o
c
o
2
1H NMR data for
I and II in CDCl3 are given in Taꢀ
CH and CH2 groups from adamantane are identified
in the range of 2.00–1.50 ppm.
ble 4, where the data for ligands are also provided for
comparison. Singlet peaks at 14.46–12.74 ppm for
ligands and complexes are assigned to the phenolic hyꢀ
droxyl protons. Because of intramolecular hydrogen
In order to ensure the stability of complexes in presꢀ
ence of polar solvent, such as DMF, a 1H NMR titration
study was carried out by adding DMF into complexes
(complexes : DMF = 1 : 0.2/0.4/0.6/0.8/1.0, molar raꢀ
tio) in CDCl3, respectively, indicates both the complexꢀ
es were rather stable in solution of DMF during 24 h.
…
bond formation of –CH=N HO–, they are observed
in low field. Moreover, in this range, the presence of
integrated 1H for complexes indicates that phenolic
hydroxyls of ligands are not deprotonated when the
complexes are formed. The preservations of phenolic
hydroxyls also can be confirmed by the corresponding
IR spectra. The peaks at 8.19–7.70 ppm are assigned
to the –CH=N proton. The aromatic hydrogens are a
In each asymmetric unit of two complexes crystals
and II, zinc atom lies on a twofold rotation axis and
I
is fourꢀcoordinated via two chlorine atoms and two
oxygen atoms from the Schiff base ligands, forming a
distorted tetrahedral geometry with the smallest
set of multiplets in the range of 7.27–6.24 ppm. The angle of O(1)Zn(1)Cl(2
A) 99.19(9)° for I and
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374
JIN et al.
Table 2. Selected bond length (Å) and angles (deg) in
I
and II*
Bond
d
, Å
Bond
d
, Å
Bond
d, Å
I
Zn(1)–O(1)
Zn(1)–Cl(1)
1.974(3)
2.2273(13)
N(1)–C(7)
N(1)–C(9)
1.300(4)
1.482(5)
O(1)–C(1)
Cl(1)–C(4)
1.312(5)
1.731(2)
II
Zn(1)–O(1)
Zn(1)–Cl(1)
1.957(3)
2.2342(12)
N(1)–Cl(1)
N(1)–C(10)
1.283(6)
1.462(6)
O(1)–C(3)
O(2)–C(5)
1.312(4)
1.350(5)
Angle
ω
, deg
Angle
ω
, deg
Angle
ω, deg
I
O(1)iZn(1)O(1)
O(1)iZn(1)Cl(2)
O(1)Zn(1)Cl(2)
Cl(2)iZn(1)Cl(2)
111.91(18)
99.19(9)
113.65(9)
119.89(7)
C(7)N(1)C(9)
N(1)C(7)C(6)
O(1)C(1)C(2)
O(1)C(1)C(6)
122.4(3)
123.59(17)
122.6(3)
119.4(3)
N(1)C(9)C(8)
N(1)C(9)C(10)
C(1)O(1)Zn(1)
109.3(4)
110.3(3)
130.3(3)
II
O(1)iZn(1)O(1)
O(1)iZn(1)Cl(1)
O(1)Zn(1)Cl(1)
Cl(1)iZn(1)Cl(1)
C(1)N(1)C(10)
92.84(17)
113.88(9)
109.08(9)
115.89(7)
127.4(5)
C(3)O(1)Zn(1)
C(5)O(2)C(8)
N(1)C(1)C(2)
O(1)C(3)C(2)
130.9(3)
118.4(4)
125.6(4)
122.2(4)
C(1)C(2)C(7)
C(3)C(2)C(7)
O(1)C(3)C(4)
O(1)C(3)C(2)
119.3(4)
118.5(4)
122.8(3)
118.5(4)
i
* Symmetry code: –
x, –y
+ 2,
z.
Table 3. Main IR data for ligands and complexes (cm–1
)
Compound
ν
(C=N)
ν
(C–O)
ν
(C–H)*
ν
(O–H)
ν(M–O)
L1
1632 m
1648 s
1623 s
1643 s
1279 w
1235 m
1221 s
2849 m
2850 m
2845 s
3433 m
3449 w
3435 w
3434 w
I
483 w
496 w
L2
II
1214 m
2849 m
* Adamantane ring C–H.
O(1)Zn(1)O(1
angle of Cl(2 )Zn(1)Cl(2) 119.89(7)
O(1)Zn(1)Cl(2 ) 113.88(9) for II. The two phenyl
rings are in the intersecting planes with a dihedral angle
of 45.1(3) for and 75.3(3) for II. The shortest distancꢀ
es between two adamantanyl carbons from two ligands
are C(11)–C(11 ) 9.724 for and C(12)–C(12
6.714 for II, indicating transꢀcoordination of two
ligands to zinc (Fig. 1). They are structurally very simꢀ
ilar to another zinc(II) complex reported in [6]. The
crystal structures also involve strong O–H···N inꢀ
tramolecular hydrogen bonds between the imino N
and phenol O atoms, which benefit to stabilize the
A
) 92.84(17)
°
for II, the biggest
The thermal gravimetric analysis was carried out
with a heating rate of 20
C min–1 in an argon atmoꢀ
sphere over a temperature range of 25–800 C. The
TG–DTG curves of and II are in Fig. 4. The quite
similar thermal decomposition appearances for and
II were observed with roughly two stages. The starting
decomposition and weight loss for two complexes were
approximately 220 C and the second rapid weight loss
stages took place at approximately 330 C. When the
complexes were heated above 550 C, the residues were
deduced as oxides.
A
°
for and
I
°
A
°
°
I
°
I
°
I
A
Å
I
A)
Å
°
°
°
Two Schiff bases ligands and their zinc complexes
were studied against a gram positive and a gram negaꢀ
tive bacterium by inhibition zone method [22]. The
compounds were prepared with four concentrations of
…
…
complex structures. The distances of H O and N O
are 1.98 and 2.628 for , 1.92 and 2.590 for II. The
hydrogen bond angles of O–H···N are 132 for and
134 for II
Å
I
Å
°
I
1.0
× × × ×
10–1, 1.0 10–2, 1.0 10–3, 1.0 10–4 mo1 L–1
°
.
in DMF. The diameters of inhibition zone were meaꢀ
sured after 48 h and the results are presented in Table 5.
Complex
hydrogen bonding nor
stacking. The complexes molecules are regularly arꢀ
I
and II are found neither intermolecular
π–π
interactions existences in
All the complexes demonstrated superior antibacꢀ
ranged by weak van der Waals forces to construct a net terial activities against Escherichia coli and
structure containing adamantine cages (Figs. 2 and 3). Bacillus subtilis comparing with the corresponding
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SYNTHESIS, CHARACTERIZATION, AND ANTIBACTERIAL ACTIVITY
375
(a)
C(8)
C(16)
C(9)
C(7)
N(1
)
C(5)
Cl(1
)
C(17)
C(19)
C(14)
C(6)
C(10)
C(11)
C(4)
C(15)
C(18)
C(1)
C(12)
Cl(2
C(3)
O(1
)
)
Zn(1
)
C(13)
C(2)
Cl(2A)
C(2A)
C(13
A
)
O(1
C(1
C(6
A)
C(3A)
C(14A)
A
)
C(15
C(11
C(10
A
)
C(4A)
A)
N(1A)
C(19A)
C(12
A
)
A)
A)
C(18
A)
C(5A)
Cl(1A)
C(7A)
C(9A)
C(17A)
C(16A)
C(8A)
(b)
O(2)
C(7)
C(6)
C(2)
C(8)
C(5)
C(4)
C(1)
N(1)
C(10)
C(3)
O(1)
Cl(1)
C(20A)
C(13A)
C(19)
C(17A)
C(12A)
C(15)
Cl(1A)
C(14A
)
Zn(1)
C(16)
C(11)
C(18)
C(14)
C(9)
C(11A)
C(18
A)
C(16A)
C(9A)
C(15A)
O(1
C(3
A)
C(17)
C(12)
C(13)
C(19A)
N(1A)
C(10A)
A)
C(20)
C(4A)
C(1A)
C(8A)
C(2A)
C(5A)
O(2A)
C(7A)
C(6A)
Fig. 1. X–ray structures of I (a) and II (b). Hydrogens are omitted for clarity.
trated solution of 1.0 ×
10–1 mo1 L–1. In contrast with
complexes, the two Schiff bases demonstrated inferior
antibacterial activity under same testing conditions.
ligands; the antibacterial ability of complexes was in a
concentrationꢀdependent. It is worth to note that
complex
I showed the maximum antibacterial effect
against Escherichia coli and Bacillus subtilis in concenꢀ Especially, L1 was not found to have antibacterial acꢀ
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 40
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376
JIN et al.
, ppm; , Hz)
Table 4. 1H NMR data for ligands and complexes (
δ
J
Comꢀ
Ar–OH
CH=N
Ar–H
Ar–OCH3 N–CH
Adamantane ring–H CH3CH–N
pound
L1
3J = 8.4, 1H);
, 1H); 6.90 (
2.86 (
3J = 6.6, 1H) 1.66 (
CH2); 1.54 (
6H, CH2)
q
,
1.99 (s
, 3H, CH);
3J = 12.3, 6H,
3J = 2.7,
1.18 (d,
3J= 6.6,
3H)
13.93
8.19 (
s
, 1H) 7.26 (
7.22 (
3J = 9.3, 1H)
d
s
,
(s, 1H)
d,
q,
d,
I
13.67
, 1H)
8.12 (
s
, 1H) 7.27 (
7.23 (
7.12 (
q
,
3J = 9.0, 1H);
4J = 2.1, 1H);
3.15 (
3J = 5.7, 1H) 1.66 (
CH2); 1.55 (s
q
,
2.00 (
s
, 3H, CH); 1.32 (
3J = 11.7, 6H,
,6H, CH2)
d
,
3J= 6.6,
3H)
(
s
t
,
q,
d
,
3J = 9.0, 1H)
L2
II
14.46
, 1H)
8.01 (
s
, 1H) 7.06 (
6.37 (
3J = 8.4, 1H)
d
s
,
3J = 8.4, 1H); 3.79 (
, 1H); 6.32 (
s
, 3H) 2.82 (
3J = 6.0, 1H) 1.65 (
CH2); 1.53 (
q
,
1.97 (
3J = 12.0, 6H,
, 6H, CH2)
s
, 3H, CH); 1.17 (
d
,
3J= 6.3,
3H)
(s
d,
q,
s
12.74 7.70 (
d
,
3J= 12.9, 7.01 (
1H)
d
,
3J =9.0, 1H); 3.75 (
, 1H); 6.24 (dd
s
, 3H) 3.03 (
3J = 6.6, 1H) 1.60 (
CH2); 1.50 (
q
,
1.94 (
s
, 3H, CH); 1.28(
3J = 13.2, 6H,
, 6H, CH2)
d
,
3J=6.6,
3H)
(s, 1H)
6.93 (
s
,
q,
3J = 9.0/8.7, 1H)
s
x
0
y
Fig. 2. The packing diagram of
I
viewed along the z axis.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 40
No. 6
2014

SYNTHESIS, CHARACTERIZATION, AND ANTIBACTERIAL ACTIVITY
377
0
z
x
Fig. 3. The packing diagram of II viewed along the
y
axis.
(a)
(b)
m
, %
m
, %
100
90
80
70
60
50
40
30
20
100
90
80
70
60
50
40
30
20
10
DTG
DTG
TG
TG
100 200 300 400 500 600 700 800
T, °C
100 200 300 400 500 600 700 800
T, °C
Fig. 4. The TG–DTG curves of complexes I (a) and II (b).
Table 5. Inhibitory of compounds against bacteria growth (inhibition zone*/mm)
Bacteria name
Escherichia coli
10–2 1.0 10–3 1.0
Bacillus subtilis
10–2 1.0 10–3 1.0 10–4
×
Concentration
1.0
8.5 0.5
15.5 0.5 13.0 0.5
×
10–1 1.0
×
×
×
10–4 1.0
×
10–1 1.0
×
×
(mol L–1
)
L1
I
8.0
6.0 0.5
9.0
6.0
7.5 0.5
6.0
6.0
6.0
6.0
6.0
6.0
15.0
8.7 0.5
16.0
10.3 0.5
8.3 0.5
11.3 0.5
7.0
L2
II
7.7 0.5
12.0
7.0
6.0
6.7 0.5
7.8 0.5
6.7 0.5
6.0
11.0
7.5 0.5
6.0
* Filter paper diameter being 6.0 mm.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 40
No. 6
2014

378
JIN et al.
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ACKNOWLEDGMENTS
This work was financially supported by Foundation
of Liaoning Provincial Department of Education Inꢀ
novation Team Projects (LT2012001), the Cause of
Public
Welfare
Scientific
Research
Fund
(2012004001), Shenyang Science and Technology
Plan Project (F13ꢀ289ꢀ1ꢀ00), Liaoning University
Foundation of 211 Project for Innovative Talents
Training and the Technology Major Projects Research
Foundation (2011ZX09102ꢀ007ꢀ02), China.
vol. 13, no. 4, p. 768.
13. Naumann, C.F., Prijs, B., and Sigel, H., Eur. J. Biochem.
1974, vol. 41, no. 2, p. 209.
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