Synthesis, characterization, and structure of a silver(I) compound with thymine

Article abstract of DOI:10.1080/15533174.2011.610092

The interaction of [Ag(PPh₃)₂(CH₃COO)] (1) with thymine led to the displacement of the acetate ligand forming the mononuclear compound [Ag(PPh₃)₂(C₅H ₅N₂O₂)] (2). This compound has been characterized by IR, NMR, element analysis, and X-ray crystallographic analysis. Crystal structure of 2 shows each Ag ion is three-coordinated by two P atoms of the triphenylphosphino ligands and one N atoms of the thymine, which is stabilized by two intermolecular N-H...O and O-H...O hydrogen bonding interactions. Copyright Taylor & Francis Group, LLC.

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Synthesis, Characterization, and Structure of a Silver(I)
Compound With Thymine
Ping-Sheng Nong a , Yi-Feng Zhou a , Li-Hong Huang a , Ji-Dong Lou a , Xiao-Hong Chen b &
Xiu Lian Lu a
a College of Life Sciences, China Jiliang University , Hangzhou , Zhejiang , P. R. China
b State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical
Technology , Beijing , P. R. China
Accepted author version posted online: 14 Mar 2012.Published online: 24 Apr 2012.
To cite this article: Ping-Sheng Nong , Yi-Feng Zhou , Li-Hong Huang , Ji-Dong Lou , Xiao-Hong Chen & Xiu Lian Lu (2012)
Synthesis, Characterization, and Structure of a Silver(I) Compound With Thymine, Synthesis and Reactivity in Inorganic, Metal-
Organic, and Nano-Metal Chemistry, 42:3, 313-316, DOI: 10.1080/15533174.2011.610092
To link to this article: http://dx.doi.org/10.1080/15533174.2011.610092
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 42:313–316, 2012
Copyright ꢀ Taylor & Francis Group, LLC
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ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2011.610092
Synthesis, Characterization, and Structure of a Silver(I)
Compound With Thymine
Ping-Sheng Nong,1 Yi-Feng Zhou,1 Li-Hong Huang,1 Ji-Dong Lou,1 Xiao-Hong
Chen,2 and Xiu Lian Lu1
1College of Life Sciences, China Jiliang University, Hangzhou, Zhejiang, P. R. China
2State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology,
Beijing, P. R. China
EXPERIMENTAL
The interaction of [Ag(PPh3)2(CH3COO)] (1) with thymine led
to the displacement of the acetate ligand forming the mononuclear
Materials and Physical Measurements
All reagents and chemicals were purchased commercially
compound [Ag(PPh3)2(C5H5N2O2)] (2). This compound has been
characterized by IR, NMR, element analysis, and X-ray crystal-
lographic analysis. Crystal structure of 2 shows each Ag ion is
three-coordinated by two P atoms of the triphenylphosphino lig-
ands and one N atoms of the thymine, which is stabilized by two
intermolecular N-H. . .O and O-H. . .O hydrogen bonding interac-
tions.
and used without further purification, and all water used in
experiments was doubly distilled. Infrared (IR) spectra were
recorded on a TJ270–30A spectrometer (Tianjin) in KBr pellets
1
1
in the range of 400–4000 cm−1. H NMR and 31P{ H} NMR
spectrum were measured in d6-DMSO on Avance 400 MHz
(Bruker) spectrometer. Elemental analyses were carried out on
a Perkin-Elmer 2400II elemental analyzer.
Keywords hydrogen bond, phosphines, silver, thymine
The diffraction data were collected on a Bruker APXE II
diffractometer equipped with a graphite-monochromatized Mo
Kα radiation (λ = 0.71073 Å) up to a 2θ limit of 54.88◦ 2 at
296(2) K. Data intensity was corrected by Lorentz-polarization
factors and empirical absorption. The structure was solved by di-
rect methods and expanded with difference Fourier techniques.
All non-hydrogen atoms were refined anisotropically. Except
the hydrogen atoms on oxygen atoms, the other hydrogen atoms
were generated geometrically. All calculations were performed
with the SHELXTL-97 package. The crystallographic data and
structural refinement are summarized in Table 1, the selected
bond lengths and bond angles are listed in Table 2.
INTRODUCTION
The coordination and supramolecular chemistry of silver(I)
compounds received increasing interest due to their antiethylene
and antimicrobial activities.[1–6] It is noted that metal complexes
of nucleobases are very important in nucleic acid processes and
in the development of antitumor therapies.[7–11] Based on these
reasons and in continuation of our work on Ag compounds with
diphosphine ligand of dppf.[12,13] we wished to synthesize a se-
ries of Ag(I) derivatives containing mixed ligands of phosphines
and nucleobases, which may have the same interesting activi-
ties. Thymine may offer three coordination sites, N1, O1, and
O2, of which the amino hydrogen atom is used to be displaced
by silver ion in neutral or alkaline solution. Herein, we describe
the preparation, characterization, and molecular structure of the
phosphinesilver(I) compound with thymine.
Synthesis
[Ag(PPh3)2 (CH3COO)] (1)
[Ag(PPh3)2(CH3COO)] (1) was easily prepared by slightly
modifying the literature procedure.[14] PPh3 (0.9428 g, 3.595
mmol) and AgAc (0.3000 g, 1.797 mmol) in 2:1 molar equiva-
lents were added in mixed solvents of C2H5OH -H2O (30 mL:30
mL), the solution with shielding from light was warmed at 70◦C
for 5 h gave a transparent liquid. After cooling, evaporation
of the solution and washed with diethyl ether to give the col-
Received 1 July 2011; accepted 31 July 2011.
The authors are grateful to the Project of the National Ministry
of Education (000049)and Ministry of Personnel(01017-080002), the orless residual solids. Yield 1.1111 g, 89%. Anal. Calcd. for
C37H33P2AgO2: C, 66.0; H, 4.8; Found (%): C, 66.1; H, 4.9. 1H
State Key Laboratory of Chemical Resource Engineering (Beijing Uni-
versity of Chemical Technology) and Qianjiang Project of Zhejiang
NMR (CD3OD, ppm): δ 1.90 (s, 3H, CH3), 7.37 - 7.49 (m, 30H,
Province (01002-123-080050) for financial support.
Address correspondence to Xiu Lian Lu, College of Life Sciences,
China Jiliang University, Hangzhou, Zhejiang 310018, P. R. China.
E-mail: luxiulian@yahoo.com.
1
Ph). 31P{ H} NMR (CD3OD): δ 11.30 (s). IR (KBr, cm−1): ν
3444w, 3062w, ν (CO) 1650w, 1552s, 1480s (Ar), 1435s (Ar),
1400s, 1335m, 1309w, 1186w, 1158w, 1098w, 1072w, 1028w,
313

314
P.-S. NONG ET AL.
7 and 8. The resulting mixture was heated at 70◦C for 2 h. Af-
TABLE 1
Selected bond lengths (Å) and angles (◦) for 2
ter cooling, the resultant suspension was filtered to collect an
insoluble colorless precipitate, which was washed with diethyl
ether and dried in vacuo. Yield 0.0305 g (37%). Anal. Calcd. for
C42H39N2P2O3Ag: C, 63.8; H, 5.0; N,3.5; Found (%):C, 63.7;
H, 5.1; N, 3.5. 1H NMR (d6-DMSO, ppm): δ 1.69 (s, 3H, CH3),
3.16 (s, 1H, CH), 7.33–7.40 (m, 25H, Ph), 7.45–7.48 (m, 5H,
[Ag(PPh3)2] C5H5N2O2·CH3OH
Bond lengths
Ag1-P1
Ag1-P2
Ag1-N1
O1-C13A
O2-C5
2.4513 (10)
2.4544 (10)
2.2361 (26)
1.2519 (40)
1.2412 (42)
1.3369 (43)
1.3525 (44)
1.3711 (40)
1.3488 (43)
1.3389 (50)
1.4543 (47)
1.5069 (49)
1
Ph). 31P{ H} NMR (d6-DMSO): δ 7.19 (s). IR (KBr, cm−1):
3444w, ν (NH) 3058w, ν (CO) 1638s, ν (C N) 1547s, ν (NH)
1494m, ν (C N) 1485s, 1434s, 1414s, 1360w, 1294w, ν (C-N)
1181w, 1098m, 1030w, 1000w, 890w, 787m, 744s, 696s, 589w,
ν (Ag-N(ligand)) 509s.
N1-C13A
N1-C5
Diffraction-quality crystals of 2·MeOH was obtained by slow
crystallization of the complex from CH3OH-H2O after five days
at room temperature.
N2-C13A
N2-C15A
C19A-C15A
C19A-C5
C19A-C11
RESULTS AND DISCUSSION
Bond angles
Synthesis
P1-Ag1-N1
P1-Ag1-P2
P2-Ag1-N1
Ag1-N1-C5
Ag1-N1-C13A
C13A -N1-C5
N1-C5-O2
N1-C5-C19A
O2-C5-C19A
C5-C19A-C11
C5-C19A-C15A
C15A-C19A-C11
C19A- C15A -N2
C15A -N2-C13A
N2-C13A-O1
N2-C13A-N1
O1-C13A-N1
117.50 (8)
128.33 (4)
114.12 (8)
119.34 (22)
118.47 (21)
112.16 (27)
118.67 (31)
119.00 (31)
112.33 (33)
119.83 (33)
116.74 (30)
123.34 (32)
112.15 (29)
121.24 (29)
119.47 (30)
118.70 (29)
121.84 (28)
Compound 1 is readily obtained in high yield by reaction of
Ag(CH3COO) and PPh3 in 1:2 molar ratio. Quality diffraction
crystals of 1 was unexpectedly obtained from recrystallization
of complex 2 in MeOH/diethyl ether, its structural data is con-
sistent with the values reported by Ng and Othman in 1997.[14]
Unfortunately, their report does not include the spectral proper-
ties. In the IR spectrum, the characteristic band at 1650 cm−1
is assigned to ν(C O) group of acetate ligands. The 1H NMR
spectrum displays an intense singlet at δ 1.9 ppm and a multiplet
at δ 7.37–7.49 ppm due to –CH3 of acetate and phenyl protons
1
of PPh3, respectively. 31P{ H} NMR spectrum shows only one
resonance at δ 11.3 ppm, consistent with its solid-state structure.
Repeated attempts to prepare compound 2 by treating com-
pound 1 and thymine in hydrothermal method were largely un-
successful and gave black solids, which are insoluble in the
polar and chlorinated solvents. However, the equimolar reac-
tion between 1 and thymine in CH3OH-H2O solvents yielded
compound 2 as white precipitates. In this reaction, it is nec-
essary to add a base for this reaction to remove the produced
CH3COOH, indicating that the product toward hydrolysis with
CH3COOH is not robust. At elevated pH, the amino hydrogen
atom of thymine is deprotonated and coordinated with Ag atom,
998m, 918w, 768m, 745s, 696s, 658m, 618w, 515s, 501s, 440w,
419w.
[Ag(PPh3)2(C5H5N2O2)] (2)
A mixture of 1 (0.0691 g, 0.100 mmol) and thymine (0.0126 instead of displacing PPh3 as ligand to form silver complex con-
g, 0.100 mmol) in 1:1 molar ratio was dissolved in mixed sol- taining both thymine ligand and acetate anion. Because silver is
vents of CH3OH-H2O (10 mL:10 mL), and to this solution was a hard atom and as such would be expected to react with nitrogen
added a solution of sodium hydroxide to adjust the pH between donor over an oxygen atom, and thus are available for acetate
TABLE 2
´
Hydrogen bonds for 2 (Å and ◦)
D-H
O3-H3
N2-H2B
d(D-H)
0.835
0.860
d(H..A)
1.881
1.932
<DHA
174.52
166.88
d(D..A)
2.713
2.776
A
O2
O1
symmetry codes
[-x+1, -y+1, -z+1]

PHOSPHINE SILVER(I) COMPOUND WITH THYMINE
315
ligand replacement in compound 1, resulting in the formation of geometry because of the lack of electron donor. The distances
´
´
2. Compound 2 is soluble in methanol and ethanol, and is stable
and shows no sensitivity to the light as solids and in solution
at room temperature. IR spectrum of 2 shows the characteristic
bands at 3058 and 1494 cm−1 are due to ν(N-H) stretching and
bending vibration. Two strong bands at 1547 and 1485 cm−1 are
assigned to ν(C N) stretching frequencies. A strong and sharp
band at 1638 cm−1 is related to the ν(C O) stretching vibration
for the carbonyl groups, which is shifted about 38 cm−1 toward
lower wave numbers in caparison to the free thymine ligands
of Ag-P (Ag–P1 2.4513 (10) Å, Ag–P2 2.4544 (10) Å) are not
different from the reported Ag(PPh3) complexes (e.g., 2.436 (3)
´
Å, 2.432 (2) Å in [Ag(R,S-Hpyrrld)(PPh3)2],[16] 2.6026 (8) Å,
´
´
2.5441 (7) Å, and 2.5432 (7) Å in AgOCOC2F5·PPh3·0.5thf).[17]
´
However, the Ag-N distance (2.2361 (26) Å) is significantly
longer than those reported Ag(I) complexes with nucleobases
´
(AgNO3·9-methyladenine, 2.08–2.11 Å[18]; Ag(C5H5N2O2),
´
2.08(3) Å).[19] The bond lengths of C O and C C double
1
(1676 cm−1). The H NMR spectrum displays signals of the
´
bond are 1.2519(40), 1.2412(42), and 1.3389(50) Å, respec-
tively. Another feature of interest is the bond length of single-
bond character present in C13A-N1 bond, which exhibits par-
methyl group CH3 and CH as a singlet, respectively, and the
phenyl protons of PPh3 ligands as two multiplets. We note but
1
cannot explain the absence of the NH proton. The 31P{ H} NMR
´
tial double-bond character (1.3369(43) Å), close to those of
spectrum gives only one relatively sharp signal at δ 7.19 ppm,
shifted to the low field as compared with δ 11.3 ppm in complex
1, and may be due to that oxygen atom is more electronegative
than that of nitrogen atom. Solid-state emission spectra of free
thymine, and compounds 1 and 2 have been investigated at room
temperature as well, however, the results exhibit that these two
silver(I) complexes unfortunately emit no photoluminescence,
in agreement with those reported Ag(I) complexes with weak
photoluminescence.[15]
[CpRu(dppf)(S2CNEt2)2].[20] The sum of angles at Ag is 359.95◦
(P1- Ag1 – N1, 117.50(8)◦; P1- Ag1 – P2, 128.33(4)◦; P2- Ag1
– N1, 114.12(8)◦), indicating that Ag, P1, P2, and N3 are copla-
nar. The same coplanar cases were found in the ring of thymine,
as the sum of angles at C13A and C19A are 360.01◦ (N1-
C13A-O1 121.84(28)◦, O1-C13A-N2 119.47(30)◦, N1-C13A-
N2 118.70(29)◦), and 359.91◦ (C5-C19A-C11 119.83(33)◦, C5-
C19A-C15A 116.74(30)◦, C11-C19A-C15A 123.34(32)◦), re-
spectively. Moreover, the conformation stabilized by secondary
bonding interactions were observed as shown in Figure 2. The
hydrogen bonds data are summarized in Table 3. The intermolec-
ular hydrogen bonds exist between N-H of one thymine and O
atom of another thymine with N. . .O and O. . .H distances of
2.713 and 1.881 Å and an N-H. . .O angle of 166.88◦, another in-
termolecular hydrogen bond O-H. . .O occurs between methanol
solvates and thymine, with O. . .O and O. . .H distances of 2.776
and 1.932 Å and an O-H. . .O angle of 174.52◦, in which this
interaction must be considered very strong (sum of the covalent
X-Ray Crystal Structure
[Ag(PPh3)2(C5H5N2O2)] (2)·CH3OH
The molecular structure of compound 2 is shown in Figure 1,
compound 2 is mononuclear, crystallizes in the P-1 space group,
in which the silver atom is three-coordinated with two phos-
phines and one thymine ligand and exhibits 16e trigonal planar
FIG. 2. Hydrogen bonding interactions in 2.
FIG. 1. ORTEP’s molecular structure of 2.

316
P.-S. NONG ET AL.
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[Ag(PPh3)2C5H5N2O2]
·CH3OH
Compound
Empirical formula
Formula weight
Temperature (K)
Crystal system
Space group
a (Å)
C42H39N2P2AgO3
789.5944
296(2) K
Triclinic
P-1
10.454(2)
10.494(2)
17.580(4)
98.73(3)
b (Å)
c (Å)
α (◦)
β (◦)
91.39(3)
95.16(3)
γ (◦)
´
V (Å3)
1897.3(7)
Z
2
1.382
0.656
Dc(g·cm−1
)
µ(mm−1
F(000)
)
812
Reflections collected
18186 / 8480
8480 [R(int) = 0.0259]
97.7%
Independent reflections
Completeness to theta = 27.53
Data / restraints / parameters
goodness-of-fit on F2
8480 / 1 / 455
1.140
Final R indices[I>2σ (I)]
R indices (all data)
Largest diff. peak and hole
R = 0.0395, wR = 0.1174
R = 0.0509, wR = 0.1304
1.075,-0.413
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