33 卷 10 期
2014. 10
结
构 化 学 （JIEGOU HUAXUE）
Chinese J. Struct. Chem.
Vol. 33, No. 10
1527─1532
Synthesis, Crystal Structure and
Properties of a Copper Complex with the
Bicycle[2.2.1]-2-heptene-5,6-dicarboxylic Acid①
LI Weia, b
LI Chang-Hongc
LI Heng-Fenga② TAN Xiong-Wena, b
a
(School of Materials Science and Engineering,
Central South University, Changsha 410083, China)
b
(Department of Chemistry and Materials Science,
Hengyang Normal University, Hengyang 421008, China)
c
(Department of Chemical Engineering, Hunan Institute of Technology, Hengyang 421002, China)
ABSTRACT
A new copper complex 2{Cu(C10H8N2)[C8H11O2(COO)](H2O)3}·(H2O)5 with
bicycle[2.2.1]hept-2-en-5,6-dicarboxylic acid (H2L) [C7H8(COOH)2], basic copper carbonate and
2,2΄-bipyridine has been synthesized in the mixed solvents of methanol and water. It crystallizes in
the triclinic system, space group P 1 , with a = 7.4626(5), b = 11.9779(8), c = 12.9841(8) Å, α =
109.7040(10), β = 98.7550(10), γ = 90.6240(10)º, V = 1077.50(12) Å3, Dc = 1.538 g/cm3, Z = 1,
F(000) = 520, GOOF = 1.065, R = 0.0360 and wR = 0.0950. The copper ion is coordinated with four
oxygen atoms from one H2L molecule and three water molecules together with two nitrogen atoms
from the 2,2΄-bipyridine molecule, forming a distorted octahedral coordination geometry. The
thermal stability and electrochemical properties were also studied.
Keywords: copper(II) complex, crystal structure, properties analysis
1
ligands have recently been reported[3], copper com-
INTRODUCTION
plexes with flexible carboxylic acid, especially
Copper is one of the important elements of life,
flexible various unsaturated carboxylic acids and
and its complexes with organic acids widely exist in
second ligand complexes, have been scarcely explo-
the life system, which has special biological
red[4]. In order to research the structures and pro-
activities and catalysis[1]. Simulation synthesis of the
perties of copper complexes with various unsatura-
life system of copper(II) complexes with organic
ted organic carboxylic acids and further enrich the
acid formation and the studies on the relation of
model copper complexes, a new copper(II) complex
structures and properties of the complexes are of
2{Cu(C 10 H 8 N 2 )[C 8 H 11 O 2 (COO)](H 2 O) 3 }·(H 2 O) 5
great significance to reveal the structure of metal
with bicycle[2.2.1]hept-2-en-5,6-dicarboxylic acid
[2]
enzyme and understand the life phenomena .
(H2L) and 2,2΄-bipyridine has been synthesized, and
Despite the fact that a great number of copper com-
its structure was characterized by X-ray diffraction
plexes with aromatic carboxylic acids and second
analysis. The thermal stability and electrochemical
Received 20 December 2013; accepted 17 July 2014 (CCDC 976858)
①
Supported by the Natural Science Foundation of Hunan Province (No.11JJ9006), Key Project of Science and Technology Plan
of Hunan Province (2012FJ2002) and the Construct Program of the Key Discipline in Hunan Province
②
Corresponding author. E-mail: [email protected]
LI W. et al.: Synthesis, Crystal Structure and Properties of a Copper
Complex with the Bicycle[2.2.1]-2-heptene-5,6-dicarboxylic Acid
1528
No. 10
properties of the complex were also studied. The
considered to be observed (I > 2σ(I)) and used in the
result shows that the electron transfer in the elec-
succeeding
trolysis is quasi-reversible. In addition, the complex
performed using SHELXS-97 and SHELXL-97[6].
is stable under 80 ℃.
The final refinement including hydrogen atoms was
refinement.
All
calculations
were
converged to R = 0.0360, wR = 0.0950 (w = 1/[σ2(Fo2)
2
+ (0.0422P)2 + 1.7713P], where P = (Fo2 + 2Fc2)/3),
EXPERIMENTAL
(∆/σ)max = 0.001, S = 1.065, (∆ρ)max = 409 and
2. 1
Reagents and instruments
(∆ρ)min = –502 e·nm-3.
H2L was prepared by ourselves[5], the other materials were of analytical grade and used without
3 RESULTS AND DISCUSSION
further purification. Crystal structure was determined on a Bruker SMART APEX CCD diffractometer.
3. 1 Crystal structure of the complex
Thermal stability (TG) study was executed on a
Selected bond lengths and bond angles are shown
PRT-2 Pyris1 instrument in air. Electrochemical
in Table 1. Hydrogen bond lengths and bond
experiment was carried out using an EC550 (Wuhan
angles are listed in Table 2. The crystal structure of
Gaoshi Ruilian Company).
the title complex is revealed in Fig. 1, and its
2. 2 Synthesis of the complex
packing diagram in Fig. 2. As shown in Fig. 1, the
2 mmol H2L (0.364 g) and 2 mmol of basic
whole unit consists of one copper ion, H2L and 2,2′-
copper carbonate (0.478 g) were added into 20 mL
bipyridine together with coordinated and free water
of methanol and water (v:v = 5:1) and stirred at 55～
molecules. The central copper ion is coordinated
60 ℃ for about 4.0. Then 2 mmol 2,2΄-bipyridine
with two nitrogen atoms from 2,2΄-bipyridine, one
(about 0.312 g) was added and mixed with the pH
oxygen atom from the H2L molecule and three
value being adjusted to 6.0～6.5 by adding dilute
oxygen atoms from water molecules, giving an
triethylamine, and then stirred at 50～60 ℃ for
octahedral coordination geometry. In the CuN2O4
about 20 h. Afterwards, the resultant solution was
octahedron, the bond angles of N(1)–Cu(1)–N(2),
filtrated, and the filtrate was kept untouched and
N(2)–Cu(1)–O(2), O(2)–Cu(1)–O(6) and O(6)–Cu(1)–
evaporated slowly at room temperature. Blue
N(1) are 79.87(9), 98.71(8), 84.92(7) and 96.46(8)º,
block-shaped single crystals suitable for X-ray
respectively, with the total to be 359.96º, indicating
diffraction analysis were obtained after two weeks.
that N(1), N(2), O(2), O(4) and Cu(I) are almost
-1
Yield: 36.4%. IR (v/cm ): 3483(w), 3445(w),
coplanar, while O(5) and O(7) occupy the axial
3082(w), 1594(vs), 1578(vs), 1547(m), 1457(vs),
positions. The Cu–N bond lengths range from 2.054
1292(vs), 1271(m), 1182(m), 1148(m), 876(m),
to 2.070 Å, and the mean distance is 2.062 Å which
761(vs), 742(s), 700(w), 474(w).
is close to that in [CuI(2,2΄-bipy)2]{[CuII(2,2΄-bipy)2]2
2. 3 Structure determination
(BW12O40)}·4H2O,[Cu2(μ-ox)(LRR)2(CH3COCH3)2-
A single crystal with dimensions of 0.18mm ×
(ClO4)2], Cu(o-methylbenzoic acid)2(2,2΄-bipy)·(H2O),
0.17mm × 0.15mm was put on a Bruker SMART
Cu 2 (o-C6 H5 COC 6 H5 COO)4 (C 10 H8 N2 )2 (H2 O)2 and
APEX CCD diffractometer equipped with a graphi-
{[Cu(2,2΄-bipy)-(HPDA)](HPDA)(H2O)}n (Cu–N =
te-monochromatic MoKa radiation (λ = 0.71073 Å)
1.980～2.070 Å)[7]. It suggests that the complex
by using a φ-ω scan mode at 296(2) K. Corrections
coordinated with 2,2′-bipyridine is stable. The Cu–O
for Lp factors and empirical adsorption correction
bond lengths range from 2.0620 to 2.0760 Å, avera-
were applied. Out of 6288 total reflections collected
ged by 2.0696 Å. In carboxyl group participating in
in the 1.69≤θ≤25.01º range, 3785 were inde-
coordination, the bond O(1)–C(18) in 1.264(5) Å is
pendent with Rint = 0.0205, of which 3423 were
different from O(2)–C(18) in 1.258(5) Å, indicating
2014
Vol. 33
结
构
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学（JIEGOU HUAXUE）Chinese
J.
Struct. Chem.
1529
a monodentate coordination mode of H2L after
and O(8)–H(8A)⋅⋅⋅O(1) (2.667(3) Å, 161°). The
dissociating the hydroxyl hydrogen atom.
oxygen atoms in free water molecules are linked by
Fig. 2 and Table 2 show another noticeable cha-
hydrogen bonds: O(9)–H(9A)⋅⋅⋅O(8) (2.802(3) Å,
racteristic of the title complex, several hydrogen
166°) and O(9)–H(9B)⋅⋅⋅O(10) (2.767(7) Å, 152°).
bonding interactions existing between oxygen in
Hydrogen bonds contribute to the stability of the
water connected with H2L via its coordinated oxy-
compound[8].
gen atoms: O(5)–H(5A)⋅⋅⋅O(4) (2.690(3) Å, 171°)
Table 1.
Selected Bond Lengths (Å) and Bond Angles (°)
Bond
Dist.
Bond
Dist.
Bond
Dist.
Cu(1)–N(2)
2.054(2)
Cu(1)–O(5)
2.0620(19)
Cu(1)–O(6)
2.0662(18)
Cu(1)–N(1)
2.070(2)
Cu(1)–O(2)
2.0742(18)
Cu(1)–O(7)
2.0760(18)
O(1)–C(18)
1.264(3)
O(2)–C(18)
1.258(3)
O(3)–C(19)
1.254(3)
O(4)–C(19)
1.274(3)
Angle
(°)
Angle
(°)
Angle
(°)
N(2)–Cu(1)–O(5)
87.44(8)
N(2)–Cu(1)–O(6)
176.11(8)
O(5)–Cu(1)–O(6)
91.42(7)
N(2)–Cu(1)–N(1)
79.87(9)
O(5)–Cu(1)–N(1)
92.04(8)
O(6)–Cu(1)–N(1)
96.46(8)
N(2)–Cu(1)–O(2)
98.77(8)
O(5)–Cu(1)–O(2)
89.08(7)
O(6)–Cu(1)–O(2)
84.92(7)
N(1)–Cu(1)–O(2)
178.20(8)
N(2)–Cu(1)–O(7)
88.76(8)
O(5)–Cu(1)–O(7)
175.99(7)
O(6)–Cu(1)–O(7)
92.45(7)
N(1)–Cu(1)–O(7)
88.55(8)
O(2)–Cu(1)–O(7)
90.24(7)
Table 2.
Hydrogen Bond Lengths (Å) and Bond Angles (°)
D–H⋅⋅⋅A
d(D–H)
d(H⋅⋅⋅A)
d(D⋅⋅⋅A)
∠DHA
O(5)–H(5A)⋅⋅⋅O(8)a
0.85
1.87
2.722(3)
179
O(5)–H(5B)⋅⋅⋅O(4)b
0.85
1.85
2.690(3)
171
O(6)–H(6A)⋅⋅⋅O(3)b
0.85
1.84
2.691(3)
175
O(6)–H(6B)⋅⋅⋅O(4)
0.85
1.94
2.785(3)
173
O(7)–H(7A)⋅⋅⋅O(1)
0.85
1.86
2.687(3)
164
O(7)–H(7B)⋅⋅⋅O(4)c
0.85
1.88
2.692(3)
159
O(8)–H(8A)⋅⋅⋅O(1)d
0.85
1.85
2.667(3)
161
O(8)–H(8B)⋅⋅⋅O(3)a
0.85
2.04
2.830(3)
155
O(9)–H(9A)⋅⋅⋅O(8)
0.85
1.97
2.802(3)
166
O(9)–H(9B)⋅⋅⋅O(10)e
0.85
1.99
2.767(7)
152
O(9)–H(9B)⋅⋅⋅O(10)f
0.85
1.86
2.676(7)
160
Symmetry codes: (a): 1–x, 1–y, 1–z; (b): 1–x, 1–y, –z; (c):
–x, 1–y, –z; (d): –x, 1–y, 1–z; (e): –1+x, y, z; (f):1–x, –y, 1–z
Fig. 1. Molecular structure of the title complex
Fig. 2. Hydrogen bond linking of the neighboring molecules
LI W. et al.: Synthesis, Crystal Structure and Properties of a Copper
Complex with the Bicycle[2.2.1]-2-heptene-5,6-dicarboxylic Acid
1530
3. 2
No. 10
Thermal stability property (TG) of the title com-
Infrared spectrum of the complex
The wide adsorption peaks at about 3483 and
-1
pound was executed on a PRT-2 pyris1 instrument in
3445 cm are the characteristic peaks of OH group
air atmosphere (Fig. 3). There are three weight-loss
-1
in H2O. Two strong peaks at 1578 and 1292 cm
stages from room temperature to 600 ℃. The first
could be assigned to the vas(coo-) and vs(coo-) stretching
stage occurs at 80～200 ℃ with weight loss of
vibration of H2L ligand. In addition, Δvcoo- (Δvcoo- =
19.88%, corresponding to the removal of three water
-1
vas(coo-) – vs(coo-)) of the complex, 286 cm , was
-1
greater than 200 cm , which
molecules (theoretical value is 19.86%). The second
indicates that car-
stage takes place from 200～300 ℃ with weight loss
boxylic radicals in the ligand of H2L coordinate with
of 31.40% due to the departure of one 2,2΄-bipy-
copper ions in a monodentate manner. The charac-
ridine molecule (theoretical value is 31.40%). The
teristic absorption peaks of 2,2΄-bipyridine in the
third stage is observed at 300～420 ℃ with weight
-1
complex shift to 1566, 1493 and 772 cm from 1580,
-1
loss of 48.21% resulting from the release of one
1463 and 760 cm , respectively. This reveals that
H2L molecule (theoretical value is 48.32%),
the nitrogen atom in 2,2΄-bipyridine also coordinates
confirming to the crystal structure. Under the air
[9]
with Cu(II) . The above analysis conforms to our
atmosphere, the final product is copper oxide with
experimental results.
the rate of about 15.66% (the theoretical value is
3. 3
15.94%).
Thermal stability property
Fig. 3. TG curve of the title complex
Fig. 4.
Cyclic voltammogram of the title complex
Based on the above analysis, the pyrolytic process
electrode as the auxiliary electrode, SCE as the
of the complex may be divided into the following
reference electrode, DMF as solvent, and HAc-
stages:
NaAc as the buffer solution. The experimental result
2{Cu(C10H8N2)[C8H11O2(COO)](H2O)3}·(H2O)5
demonstrated no redox peak in the two liagnds by
⎯⎯ ⎯
⎯→ 2Cu(C10H8N2)[C8H11O2(COO]
200 ~ 300℃
⎯⎯ ⎯⎯→ 2Cu[C8H11O2(COO)]
420℃
⎯300
⎯~⎯
⎯→ 2CuO
the cyclic scanning at room temperature and at 0.100
80 ~ 200℃
3. 4
Cyclic voltammogram (CV) of the complex
V/s within –0.200～1.400 V, and only a pair of
redox peaks occurred in the title complex (concentration = 3.0 × 10-6 mol/L). The potentials of its
Fig. 4 is the cyclic voltammogram of the title
anodic and cathodic peaks are as below: Epa = 0.680,
complex. Cyclic voltammograms of ligand 2,2΄-
Epc = 0.449 V, ΔE = 0.231 V, suggesting that the
bipyridine, H2L and the complex were determined
electron transfer in the electrolysis was quasi-rever-
using a three-electrode system, with the glassy
sible[10].
carbon electrode as the working electrode, platinum
2014
Vol. 33
结
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J.
Struct. Chem.
1531
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