Synthesis, structure and antimicrobial study of N-salicylidene- phenylpropanolamine bicopper(II) complex

Article abstract of DOI:10.1080/15533170600962489

A new bicopper (II) complex [Cu₂L₂Cl ₂·H₂O, H₂ L = C₆H _5-CH(OH)CH(CH₃)N=CH(C₆H₅-2-OH)], has been synthesized by Schiff base condensation of phenylpropanolamine with salicylaldehyde in the presence of Cu²⁺. The crystal of the complex was characterized by X-ray diffraction, IR, ES-MS spectroscopy, molar conductivity and elemental analyses. Antimicrobial activity study found that the complex was active against Candida albican, Bacillus pumilus and Bacillus coliforms. Copyright

Full text of DOI:10.1080/15533170600962489

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Synthesis and Reactivity in Inorganic, Metal-Organic,
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Synthesis, Structure and Antimicrobial Study of
N‐Salicylidene‐Phenylpropanolamine Bicopper(II)
Complex
Tong‐Tao Xu a , Xing‐You Xu b , Jian Gao c , Ming‐Yan Wang b , Lu‐De Lu a , Jia Ni d
Guo‐Xiang Xu b
&
a Materials Chemistry Laboratory , Nanjing University of Science and Technology , Nanjing, P.
R. China
b Department of Chemical Engineering , Huaihai Institute of Technology , Lianyungang, P. R.
China
c Department of Chemical Engineering , Lianyungang Technical College , Lianyungang, P. R.
China
d Central Laboratory of Shantou University , Shantou, P. R. China
Published online: 15 Feb 2007.
To cite this article: Tong‐Tao Xu , Xing‐You Xu , Jian Gao , Ming‐Yan Wang , Lu‐De Lu , Jia Ni & Guo‐Xiang Xu (2006) Synthesis,
Structure and Antimicrobial Study of N‐Salicylidene‐Phenylpropanolamine Bicopper(II) Complex, Synthesis and Reactivity in
Inorganic, Metal-Organic, and Nano-Metal Chemistry, 36:9, 667-672
To link to this article: http://dx.doi.org/10.1080/15533170600962489
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Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 36:667–672, 2006
Copyright # 2006 Taylor & Francis Group, LLC
ISSN: 0094-5714 print/1532-2440 online
DOI: 10.1080/15533170600962489
Synthesis, Structure and Antimicrobial Study of
N-Salicylidene-Phenylpropanolamine Bicopper(II) Complex
Tong-Tao Xu
Materials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing, P. R. China
Xing-You Xu
Department of Chemical Engineering, Huaihai Institute of Technology, Lianyungang, P. R. China
Jian Gao
Department of Chemical Engineering, Lianyungang Technical College, Lianyungang, P. R. China
Ming-Yan Wang
Department of Chemical Engineering, Huaihai Institute of Technology, Lianyungang, P. R. China
Lu-De Lu
Materials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing, P. R. China
Jia Ni
Central Laboratory of Shantou University, Shantou, P. R. China
Guo-Xiang Xu
Department of Chemical Engineering, Huaihai Institute of Technology, Lianyungang, P. R. China
congestion and in diet pills to control appetite[1–3] for many
A new bicopper (II) complex [Cu2L2Cl2 H2O, H2 L 5 C6H5- years. Podder reported its structure and Malone studied its che-
.
lating properties with copper(II)[4,5] Bhattacharyya studied its
Schiff bases complexes with several metals, including
nickel(II), palladium and platinum and described their for-
CH(OH)CH(CH3)N 5 CH(C6H5-2-OH)], has been synthesized
by Schiff base condensation of phenylpropanolamine with salicy-
laldehyde in the presence of Cu21. The crystal of the complex
was characterized by X-ray diffraction, IR, ES-MS spectroscopy,
molar conductivity and elemental analyses. Antimicrobial activity
mation and structure.[6] Recently, there are many of reports
study found that the complex was active against Candida albican, on PPA because it was linked to a significantly increased risk
of stroke, especially in women ages 18 to 49.[7,8] However,
information on the corresponding derivatives of the phenyl-
Bacillus pumilus and Bacillus coliforms.
propanolamine Schiff base is still very scant. The structure of
medicated active components is remolded, which is an effective
way to prepare curative medicinal substances.[9] Therefore, it is
important to develop new derivatives of PPA for potential bio-
medical applications. As part of our studies on the relationship
between structure and antimicrobial activity of compounds
with biologically active units, we have undertaken taken
investigations on N-salicylidene-phenylpropanolamine Cu(II)
complex, and the results are presented in this paper.
Keywords copper(II) complex, PPA, salicylaldehyde, crystal
structure, toxicity
INTRODUCTION
Phenylpropanolamine (PPA) has been in use as an ingredient
in many cold and cough remedies to relieve stuffy nose and
Received 27 May 2006; accepted 20 June 2006.
EXPERIMENTAL
The project was supported by the National Science Foundation of
Jiangsu Province (No. 02KJD150014) and the Key Laboratory of
Marine Biotechnology of Jiangsu Province.
Materials
All starting materials were of chemical purity. The solvents
used in the physical measurements were of analytical purity
(Nanjing Chemical Reagent Co. Ltd).
Address correspondence to Lu-De Lu, Materials Chemistry Lab-
oratory, Nanjing University of Science and Technology, Nanjing
214009, P. R. China. E-mail: xutongtao_1968@163.com
667

668
T.-T. XU ET AL.
Physical Measurements
reflections were collected with 6025 unique reflections
(Rint ¼ 0.0349). The crystal structure was solved by direct
methods and Fourier synthesis with the program SHELXS-
97[10] and refined by full-matrix least-squares techniques on F2
with the program SHELXS-97.[11] The non-hydrogen atoms
were refined anisotropically and hydrogen atoms were added
according to theoretical models. The final refinement converged
at R ¼ 0.0512 and wR ¼ 0.1249 for 4350 observed reflections
with I . 2s(I) (W ¼ 1/[s2 (F2o) þ (0.0741P)2 þ 1.4749P]
where P ¼ (F2o þ 2 Fc2)/3), S ¼ 1.039 and (D/s)max ¼ 1.675.
The largest peak and deepest hole on the final difference
Elemental analyses were determined with a Perkin-Elmer 240c
instrument. Solution electrical conductivity was measured by a
BSD-A numerical conductometer (Jiangsu, China) with solution
23
concentration of ꢀ1.0 ꢀ 1023 mol dm
in methanol at
.
297K. The cyclic voltammograms were obtained on a
CHI660 electrochemical analyzer. IR spectrum was measured
as KBr discs using a Nicolet 5DX FT-IR spectrophotometer.
The ES mass spectral measurement of the complex was
carried out on a LCQ System (Finngann MAT, USA) using
methanol as mobile phase. The spray mass spectrum and capil-
lary temperature were set at 4 KV and 2008C, respectively.
3
˚
Fourier map are 0.467 and 20.260 e/A , respectively.
.
Antimicrobial Activity Determination
Synthesis of Cu2L2Cl2 H2O
To a stirred solution of salicylaldehyde (0.122 g, 1.0 mmol)
As a preliminary screening for antimicrobial activity, agar
diffusion method described in the previous paper[12] was used.
.
and Cu(ClO4)2 6H2O (0.372 g, 1.0 mmol) in 25 ml absolute
.
Cu2L2Cl2 H2O dissolved in DMF was tested against standard
methanol, a solution of phenylpropanolamine hydrochloride
(0.187 g, 1.0 mmol) in 10 ml absolute methanol was added
dropwise. Then, sodium hydroxide (0.040 g, 1.0 mmol) was
added to the mixtures at 258C. After stirring for 3 h at 458C,
the mixture was filtered and acetonitrile (5.0 ml) was added
strains of Candida albicans CMCC (F) 98 001, Bacillus coli-
forms CMCC (B) 44 102 and Bacillus pumilus CMCC (B) 63
202. For the comparison, the antimicrobial activity of Cu
.
(ClO4)2 6H2O and PPA were also tested. Culture medium of
.
to the filtrate. The product [Cu2L2Cl2] H2O was precipitated
antibiotic medium 1 was used for Bacillus pumilus and
nutrient agar for Candida albicans and Bacillus coliforms.
Culture medium was transferred to glass plates and froze at
about 378C. After test strains were spread on the solid culture
medium surface, stainless steel tubes (7.8 ꢀ 6 ꢀ 10 mm) were
placed vertically on the surface. 0.10 ml samples with certain
concentration were injected to the steel tubes. They were
allowed to incubate at 378C for 24 h. The inhibition zone
around the disc was calculated as zone diameter in millimeters.
Blank tests showed that DMF in the preparation of the test sol-
utions does not affect the test organisms. All tests were repeated
three times and average data were taken as the final result.
as green Schiff base complex in a yield of 59% (0.2140 g).
M. P. 151.08C (dec.). Anal. Calcd. for C32 H34 Cl2Cu2N2O5
(%): C, 52.10; H, 4.69; N, 3.86; Found: C, 52.15; H, 4.63; N,
3.81. IR (cm21): 2980s n(NH); 1630 m n(C55N); 2932s
n(OH);1545, 1446 m n(aromatic ring). ES-MS: m/z
(%):376.1(100), 349.1(39) and 633.1(38). LM (CH3OH,
2
297K):136 S cm mol21. The deep-green single crystals
suitable for X-ray structure determination were obtained by
slow evaporation of the resulting filtrates for about 2 days at
ambient temperature.
.
.
Caution: Perchlorate salts of metal complexes with
organic ligands are potentially explosive. Only small
amounts of material should be prepared, and these should be
handled with caution.
RESULTS AND DISCUSSION
Crystal Structure of Complex
The selected bond distances and bond angles are summar-
ized in Table 1. The molecular structure of the title
compound and the packing diagram are shown in Figures 1
and 2, respectively. Crystal structure of the bicopper (II)
complex consists of an isolated molecule unit of Cu2L2Cl2
and H2O molecule. In an isolated molecule unit, two
hydrogen atoms of hydroxyl of salicylaldehyde were lost
during the formation of coordinate bond for the charge
balance. The asymmetrical system of hydrogen bonds breaks
up the potential centrosymmetricity of both chelate molecules.
In the molecule unit, two Cu (II) atoms are bridged by two
X-Ray Crystal Structure Determination
Crystal Data
C
32 H34 Cl2 Cu2 N2 O5, M ¼ 724.59, green crystal, dimen-
sions 0.20 mm ꢀ 0.20 mm ꢀ 0.15 mm, monoclinic, space
˚
group P21/c, a ¼ 10.224(2), b ¼ 13.675(3), c ¼ 24.632(5)A,
3
˚
b ¼ 96.197(4)8; V ¼ 3423.8(12) A , F(000) ¼ 1488, Z ¼ 4,
Dc ¼ 1.406 g/cm3,
m ¼ 1.438 mm21
,
l ¼ 0.71073 A;
˚
Largest diff. peak and hole, 0.467 and 20.260 e.A23
.
Data Collection and Refinement of the Crystal Structure
A greenblockcrystalofthe titlecompoundwithdimensionsof chlorine atoms and locate in NO2Cl2 coordination environment
0.20 mm ꢀ 0.20 mm ꢀ 0.15 mm was mounted on a glass fiber. with coordination number five and form two distorted square-
X-ray diffraction intensity data were collected on a BRUKER pyramidal. The deformation parameters t, computed on the
SMART CCD diffractometer with the graphite monochromated basis of the two maximal valency angles of the Cu(1) and
Mo 2 Ka (l ¼ 0.71073 A) radiation by using the v 2 2u scan Cu(2) atom as (a1-a2)/60[13] are 13.75% and 18.05%, respect-
˚
technique (1.66 ꢁ u ꢁ 25.008) at 293(2) K. A total of 17534 ively, indicate that Cu(1) and Cu(2) polyhedron are all close to

NEW BICOPPER(II) COMPLEX
669
TABLE 1
˚
Selected bond lengths (A) and bond angles (8)
Bond
Distance
Bond
Distance
Bond
Distance
Cl(1)-Cu(1)
Cl(2)-Cu(1)
Cu(1)-O(2)
Cu(2)-O(4)
2.2645(11) Cl(1)-Cu(2)
2.7545(14) Cu(1)-O(1)
2.7532(13)
1.376(4)
1.900(3)
1.321(5)
Cl(2)-Cu(2)
Cu(1)-N(1)
Cu(2)-N(2)
C(7)-N(1)
2.2615(13)
1.935(3)
1.935(4)
1.280(5)
2.028(3)
2.008(3)
Cu(2)-O(3)
C(1)-O(1)
Angle
(8)
Angle
(8)
Angle
(8)
Cu(2)-Cl(2)-Cu(1)
N(1)-Cu(1)-O(2)
O(2)-Cu(1)-Cl(1)
O(2)-Cu(1)-Cl(2)
O(3)-Cu(2)-O(4)
N(2)-Cu(2)-Cl(2)
N(2)-Cu(2)-Cl(1)
85.93(4)
81.65(13)
92.85(8)
O(1)-Cu(1)-N(1)
O(1)-Cu(1)-Cl(1)
O(1)-Cu(1)-Cl(2)
Cl(1)-Cu(1)-Cl(2)
N(2)-Cu(2)-O(4)
O(4)-Cu(2)-Cl(2)
O(4)-Cu(2)-Cl(1)
93.54(14)
91.37(9)
98.02(11)
91.03(4)
82.06(14)
90.09(9)
89.00(10)
O(1)-Cu(1)-O(2)
N(1)-Cu(1)-Cl(1)
N(1)-Cu(1)-Cl(2)
O(3)-Cu(2)-N(2)
O(3)-Cu(2)-Cl(2)
O(3)-Cu(2)-Cl(1)
Cl(2)-Cu(2)-Cl(1)
174.71(12)
166.46(12)
100.75(12)
93.60(15)
93.94(11)
92.68(11)
91.12(5)
85.11(9)
175.59(13)
164.76(12)
101.73(11)
square-pyramidal. All copper(II) centers are in a square-pyra- bond respectively. The individual Cu- Cl-Cu bridges formed
midal environment, with four short bonds in the basal plane by one short Cu-Cl and one long Cu-Cl bond have distinctly
formed by two trans O atoms and one N atom of the tridentate differentiated bond lengths. The short Cu-Cl bonds vary from
˚
ligand, and a bridge chloride ion. The fifth axial long bond is 2.2615(13) A to 2.2645 (11) A and the long Cu-Cl bonds
˚
˚
˚
formed by a chloride ligand which lies in the basal plane of from 2.7532(13) A to 2.7545(14) A, which are accorded with
the neighbouring copper(II) ion. The molecular dimensions the previously reported structure.[16] The Cu Cu non-
...
˚
are as expected with the aromatic C-C bond distances bonding distances is 3.438 A.
˚
between 1.360 to 1.448 A, and aromatic C-C-C bond angles
The packing diagram as shown in Figure 2 provides
between 118.2 to 121.58, almost within the normal evidence that the structure is comprised of unique hydrogen
range.[14,15] The bond length of C(7)–N(1) and C(23)–N(2) bonds. The O(2) of hydroxyl atom of PPA forms a strong intra-
˚
are 1.280A and 1.275A, belonging to the typical C55N Schiff molecular hydrogen bond with O(3) of hydroxyl of
˚
base bond, and the bond length of C(8)–N(1) and C(24)–
˚
N(2) are 1.480 A and 1.470 A, belonging to the C–N single
˚
FIG. 1. The molecular structure of the title compound.
FIG. 2. The molecular packing diagram of the title compound.

670
T.-T. XU ET AL.
TABLE 2
Hydrogen bond geometries (A, deg.)
˚
D–H ꢂ ꢂ ꢂ A
dD–H
dH ꢂ ꢂ ꢂ A dD ꢂ ꢂ ꢂ A
uDHA
O(2)–H(2A) ꢂ ꢂ ꢂ O(3)
O(4)–H(4A) ꢂ ꢂ ꢂ O(5)
O(5)–H(5B) ꢂ ꢂ ꢂ O(1)
0.850
0.850
0.850
1.774
1.813
1.988
2.623
2.660
2.812
178.09
173.80
163.22
salicylaldehyde, and the O(5) atom of the water molecule form
two intermolecular hydrogen bonds with O(1) and O(4). The
bond lengths and bond angles relevant to the hydrogen bond
are given in Table 2. Intermolecular hydrogen bonds and inter-
molecular van der waals in the title complex produced a three-
dimensional framework and stabilized the crystal structure.
FIG. 4. The ES mass spectrum of the title compound.
Spectral Characteristics
The structure of title complex was further confirmed by
spectral characteristics, as seen in Figure 3. Condensation of
all primary amine groups and carbonyl groups is confirmed by
the lack of N-H double stretching bands in the IR spectra in the
region 3150–3450 cm21 and also the characteristic presence
of strong C55N stretching bands at 1630 cm21 was noted.
The main peaks at m/z 376.1, 349.1 and 633.1 are observed
in Figure 4, corresponding to the species of [C16H16O2NCu þ
CH3CN þ H2O]þ, [C16H16O2NCu þ CH3OH]þ and [C16H16-
O2NCu þ C16H16O2NCu-Hþ]þ, respectively.
Cyclic Voltammetric Study
The measurements were carried out in solution of phosphate
buffer solution (PBS) and using a three-electrode cell in which
the copper complex modified glassy carbon electrode (marked
as MGC) was the working electrode, saturated calomel elec-
trode (SCE) was the reference electrode and platinum wire
FIG. 5. Cyclic voltammogram of the title complex at scan rate of 1 mV s21
.
FIG. 3. The IR spectrum of the title compound.

NEW BICOPPER(II) COMPLEX
671
TABLE 3
Cyclic voltammetric data of the title complex
Redox couple
Epa( V)
Epc (V)
DE (mV)
E1/2 (V)
Ipa/Ipc
DE1/2 (V)
CuIICuII/CuICuII
CuICuII/CuICuI
0.301
0.085
20.084
20.262
385
347
0.109
20.089
0.69
2.55
0.198
value was 2.55, so the electrode reaction was also a quasi-
reversible process corresponding to the redox couple of
CuIICuI/CuICuI.
TABLE 4
The diameter of inhibition zone
Diameter of inhibition zone
(mm)
Antimicrobial Activity
From the data in Table 4, it is observed that the title
.
complex, PPA and Cu(ClO4)2 6H2O exhibited antibacterial
Concentration Candida Bacillus Bacillus
(mg/ml)
Compound
albicans coliforms pumilus
activity against all test bacterial organisms. In the test range,
these compounds were more active against the strains with
increase in concentration. The highest antimicrobial activity
among the group of these complexes was observed against
Candida albicans and almost no difference in toxicity against
Bacillus coliforms among the three complexes. The title
complex showed higher activity against bacteria as compared
Title
8.0
4.0
2.0
1.0
22.5
18.4
17.2
16.9
15.3
14.8
13.0
12.5
20.0
18.8
16.4
14.8
compound
Cu(ClO4)2
8.0
4.0
2.0
1.0
19.3
19.2
16.8
12.3
15.0
14.2
13.4
13.0
14.0
13.3
12.8
11.1
.
to the metal salt Cu(ClO4)2 6H2O and PPA. The reason may
be attributed to the formation of the Schiff-base structure,
which can increase the antimicrobial activity due to their
active antibacterial and antitumor functions.[18,19]
PPA
8.0
4.0
2.0
1.0
18.7
17.6
15.3
12.0
14.8
13.3
11.0
10.6
13.8
12.5
11.4
9.3
SUPPLEMENTARY MATERIALS
Crystallographic data for the structures in this article have
been deposited with the Cambridge Crystallographic Data
Center as the supplementary publication nos. CCDC 600202
for the title complex. Copies of the data can be obtained, free
of charge, on application to CCDC, 12 Union Road, Cambridge
CB2 1EZ, UK.
was used as the counter electrode. The glassy carbon (GC)
electrode was polished with fine emery paper and aluminum
oxide powder on a chamois leather, respectively. The GC elec-
trode was washed with 0.01 M H2SO4 solution and then soni-
cated in water for 20 s after polishing. The MGC electrode
was constructed by depositing the dicopper complex on the
GC electrode through cyclic voltammetric scan in the potential
range of 20.5 to 0.6 V with scan rate of 100 mV s21 for 600 in
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