Syntheses and structures of silver(I) and palladium(II) complexes with ferrocenyl-phosphonodithiolate ligands

Article abstract of DOI:10.1515/znb-2010-0107

Coordinative interaction of [Ag(PPh₃)₂NO₃] or [Pd(MeCN)₂Cl₂] with in situ-prepared Na[FcP-(OR)S ₂] afforded 1 : 1 products [FcP(OR)S₂Ag(PPh ₃)₂] (R = Me 1,

Full text of DOI:10.1515/znb-2010-0107

Syntheses and Structures of Silver(I) and Palladium(II) Complexes
with Ferrocenyl-phosphonodithiolate Ligands
Xi-Ying Wang, Hua-Tian Shi, Qing Ma, and Qian-Feng Zhang
Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology,
Ma’anshan, Anhui 243002, P. R. China
Reprint requests to Dr. Qian-Feng Zhang. Fax: +86-555-2312041. E-mail: zhangqf@ahut.edu.cn
Z. Naturforsch. 2010, 65b, 32 – 36; received October 13, 2009
Coordinative interaction of [Ag(PPh3)2NO3] or [Pd(MeCN)2Cl2] with in situ-prepared Na[FcP-
(OR)S2] afforded 1 : 1 products [FcP(OR)S2Ag(PPh3)2] (R = Me 1, n-Pr 2) or the 1 : 2 product
[{FcP(OMe)S2}2Pd] (3). Complexes 1 – 3 were characterized by elemental analysis, mass spectrom-
etry, NMR (1H, 31P) and IR spectroscopy, as well as by X-ray crystallography. The distorted tetra-
hedral silver(I) coordination led to non-planar and distorted four-membered AgS2P rings in 1 and 2,
whereas the square-planar palladium(II) coordination resulted in four-membered co-planar PdS2P
rings in 3.
Key words: Synthesis, Crystal Structure, Ferrocenyl-dithiophosphonate, Heterobimetallic Complex
Introduction
methoxide or sodium n-proproxide. The molecular
structures of [FcP(OMe)S2Ag(PPh3)2] (1), [FcP(On-
Pr)S2Ag(PPh3)2] (2), and [FcP(OMe)S2]2Pd (3) are
also presented in this paper.
Organophosphorus-containing dithiolato-type com-
pounds are of interest due to their agricultural
and industrial applications [1, 2]. From the point of
view of coordination chemistry, dithiophosphonates
are bidentate ligands which can form stable com-
plexes with transition metal ions. Since Woollins
reported the dithiodiphosphetane disulfide [FcP(S)-
(µ-S)]2 [Fc = Fe(η5-C5H4)(η5-C5H5)] as an ana-
log of Lawesson’s reagent (LR) [AnP(S)(µ-S)]2
(An = 4-anisyl), the study of phosphonodithiolate
derivatives in the field of ferrocene chemistry has
been actively extended [3 – 5]. For example, a se-
ries of new ferrocenyl-phosphonothiolate derivatives
were successfully isolated from the reactions of
[FcP(S)(µ-S)]2 with alcohols or sodium alkoxides,
silanols, dienes, alkenes, cyanamides, aminoethanols,
and catechols [3, 6 – 11]. The typical ferrocenyl-
dithiophosphonate [FcP(OR)S2]− anions (R = alkyl,
aryl) may directly react with a range of metal ions
Experimental Section
Generals
All syntheses were performed in oven-dried glassware un-
der a purified nitrogen atmosphere using standard Schlenk
techniques. All reagents, unless otherwise stated, were pur-
chased as analysis grade and were used without further pu-
rification. [FcP(S)(µ-S)]2 [3] and Pd(MeCN)2Cl2 [12] were
prepared according to procedures described in the liter-
ature. [Ag(PPh3)2(NO3)] was obtained from the reaction
of PPh3 with AgNO3 in CH3OH : CH2Cl2 (2 : 1) solution.
NMR spectra were recorded on a Bruker ALX 300 spec-
trometer operating at 300 and 121.5 MHz for 1H and 31P, re-
spectively. Chemical shifts (δ, ppm) are reported with refer-
ence to SiMe4 (1H) and H3PO4 (31P), respectively. Infrared
spectra (KBr) were recorded on a Perkin-Elmer 16 PC FT-
IR spectrophotometer with the use of pressed KBr pellets,
and positive FAB mass spectra were recorded on a Finnigan
TSQ 7000 spectrometer. Elemental analysis was performed
using a Perkin-Elmer 2400 CHN analyzer.
(Au+, Rh+, Ni2+, Pd2+, Pt2+, Zn2+, Cd2+, Hg2+
,
Sn4+, and Pb2+), resulting in the formation of new
heterometallic complexes containing the electron-
rich and aromatic ferrocene groups [3 – 5, 8]. So far,
the use of these ferrocenyl-phosphonodithiolate lig-
ands as synthons for polynuclear metal clusters has
been largely overlooked. Here we report the reac-
tions of [Ag(PPh3)2]+ and [Pd(MeCN)2]2+ species
with [FcP(S)(µ-S)]2 in the presence of sodium
Syntheses
[FcP(OMe)S Ag(PPh ) ] (1)
2
3 2
To a slurry of [FcP(S)(µ-S)]2 (112 mg, 0.20 mmol) and
CH3ONa (22 mg, 0.40 mmol) in methanol (10 mL) was
added a solution of [Ag(PPh3)2NO3] (278 mg, 0.40 mmol)
c
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X.-Y. Wang et al. · Silver(I) and Palladium(II) Complexes with Ferrocenyl-phosphonodithiolate Ligands
Table 1. Crystal data, data collection parameters and details of the structure refinement of complexes 1 – 3.
33
1
2
3
Empirical formula
Formula weight
Color, habit
C47H42OP3S2FeAg
943.56
orange, block
0.29×0.22×0.14
monoclinic
P21/c
17.6541(3)
21.0026(4)
11.6711(2)
90
70.723(1)
90
4327.09(13)
4
1.45
1.0
296(2)
C49H46OP3S2FeAg
971.61
C22H24O2P2S4Fe2Pd
728.69
orange, block
0.26×0.19×0.12
monoclinic
P21/n
10.0083(1)
11.6216(1)
12.2022(1)
90
109.04(1)
90
1341.65(2)
2
1.80
2.2
296(2)
orange, block
0.55×0.45×0.38
triclinic
Crystal size, mm3
Crystal system
Space group
¯
P1
˚
a, A
10.4014(2)
11.4684(2)
19.7555(4)
83.727(1)
80.158(1)
76.857(1)
2254.99(7)
2
˚
b, A
˚
c, A
α, deg
β, deg
γ, deg
3
˚
Volume, A
Z
Density (calcd.), g cm−3
Absorption coefficient, mm−1
Temperature, K
1.43
1.0
296(2)
F(000), e
Radiation; λ, A
Reflections collected
1928
MoKα ; 0.71073
43066
996
728
˚
MoKα ; 0.71073
41830
MoKα ; 0.71073
12723
Independent reflections / Rint
Reflections with I ≥ 2σ(I)
Parameters refined
9933 / 0.0119
8547
497
0.034 / 0.068
1.01
+0.49 / −0.39
10334 / 0.0184
9153
514
0.031 / 0.070
1.01
+0.38 / −0.39
3063 / 0.0192
2775
153
0.025 / 0.055
1.04
+0.37 / −0.29
Final R1/wR2 indices (all data)a
Goodness of fit (GoF)b
−3
˚
Final max / min difference peaks, e A
a
2
R1 = ΣꢀFo|−|Fcꢀ/Σ|Fo|, wR2 = [Σw(Fo −Fc2)2/Σw(Fo2)2]1/2, w = 1/[σ2(Fo2)+aP2 +bP] where P = (Fo2 +2Fc2)/3, a = 0.0317 and
b = 2.0123 for 1, a = 0.0375 and b = 0.8186 for 2, and a = 0.0265 and b = 0.4332 for 3; b GoF = [Σw(Fo −Fc2)2/(Nobs −Nparam)]1/2
.
2
1
in THF (15 mL). The mixture was stirred at r. t. for 4 h. Fc), 7.23 – 7.46 (m, 30H, Ph). – 31P{ H} NMR (121.5 MHz,
The solvents were pumped off, and the residue was recrys- CDCl3): δ = 41.7 (s, 1P, PPh3), 109.2 (s, 1P, FcPS2). –
tallized from CH2Cl2/hexane to give an orange crystalline Selected IR bands (KBr, cm−1): ν(P – O – C) 1186 (m) and
solid within five days. Yield: 284 mg (76 %). – 1H NMR 1025 (s), ν(P – S) 636 (s) and 574 (s), ν(P – C) 527 (s), 511
(300 MHz, CDCl3): δ = 3.93 (d, J(P,H) = 8.46 Hz, 3H, and (s) 488 (m). – MS (FAB): m/z = 971 [M]+, 709 [M–
OCH3), 4.41 (s, 5H, C5H5 in Fc), 4.53 (m, 4H, C5H4 in PPh3]+, 447 [M–2PPh3]+. – Anal. for C49H46OP3S2FeAg:
1
Fc), 7.21 – 7.49 (m, 30H, Ph). – 31P{ H} NMR (121.5 MHz, calcd. C 60.62, H 4.77; found C 60.44, H 4.72.
CDCl3): δ = 43.2 (s, 1P, PPh3), 111.3 (s, 1P, FcPS2). – Se-
lected IR bands (KBr, cm−1): ν(P–O–C) 1189 (m) and 1027
[FcP(OMe)S ] Pd (3)
2 2
(s), ν(P–S) 633 (s) and 579 (s), ν(P – C) 523 (s) 512 (s) and
483 (m). – MS (FAB): m/z = 943 [M]+, 681 [M–PPh3]+,
To a slurry of [FcP(S)(µ-S)]2 (112 mg, 0.20 mmol) and
419 [M–2PPh3]+. – Anal. for C47H42OP3S2FeAg: calcd.
CH3ONa (22 mg, 0.40 mmol) in methanol (10 mL) was
C 59.81, H 4.49; found C 59.27, H 4.45.
added a solution of [Pd(MeCN)2Cl2] (52 mg, 0.20 mmol)
in MeCN (10 mL). The mixture was stirred at r. t. for 1 h.
The solvents were pumped off, and the residue was recrys-
tallized from CH2Cl2/hexane to give an orange crystalline
[FcP(OnPr)S Ag(PPh ) ] (2)
2
3 2
To a slurry of [FcP(S)(µ-S)]2 (112 mg, 0.20 mmol) and solid within three days. Yield: 86 mg (56 %). – 1H NMR
n-PrONa (33 mg, 0.40 mmol) in n-PrOH (5 mL) was added (300 MHz, CDCl3): δ = 3.92 (d, J(P,H) = 8.02 Hz, 3H,
a solution of [Ag(PPh3)2NO3] (278 mg, 0.40 mmol) in THF OCH3), 4.41 (s, 5H, C5H5 in Fc), 4.48 (m, 4H, C5H4 in
(15 mL). The mixture was stirred at r. t. for 6 h. The solvents Fc). – 31P{ H} NMR (121.5 MHz, CDCl3): δ = 119.5. –
1
were pumped off, and the residue was recrystallized from Selected IR bands (KBr, cm−1): ν(P – O – C) 1189 (m) and
CH2Cl2/hexane to give an orange crystalline solid within a 1027 (s), ν(P – S) 634 (s) and 574 (s), ν(P – C) 528 (s), 515
week. Yield: 273 mg (71 %). – 1H NMR (300 MHz, CDCl3): (s) and 485 (m). – MS (FAB): m/z = 728 [M]+. – Anal.
δ = 1.05 (t, 3H, CH3), 1.56 (m, 2H, CH2), 4.39 (m, 2H, for C22H24O2P2S4Fe2Pd: calcd. C 36.22, H 3.32; found
CH2O), 4.44 (s, 5H, C5H5 in Fc), 4.51 (m, 4H, C5H4 in C 36.14, H 3.29.
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34
X.-Y. Wang et al. · Silver(I) and Palladium(II) Complexes with Ferrocenyl-phosphonodithiolate Ligands
˚
Table 2. Selected bond lengths (A) and bond angles (deg) for
complexes 1, 2 and 3a.
Complexes
1 (M = Ag)
2 (M = Ag)
3 (M = Pd)
M(1)–S(1)
M(1)–S(2)
Ag(1)–P(2)
Ag(1)–P(3)
P(1)–S(1)
P(1)–S(2)
P(1)–O(1)
2.8298(5)
2.6056(5)
2.4747(5)
2.4743(5)
1.9843(7)
1.9940(7)
1.6051(14)
2.7574(6)
2.6061(5)
2.4644(4)
2.4593(4)
1.9742(7)
1.9986(6)
1.6016(16)
2.3439(5)
2.3486(6)
2.0100(7)
2.0135(7)
1.5785(14)
S(1)–Ag(1)–S(2)
P(2)–Ag(1)–S(1)
P(2)–Ag(1)–S(2)
P(3)–Ag(1)–S(1)
P(3)–Ag(1)–S(2)
P(2)–Ag(1)–P(3)
P(1)–S(1)–M(1)
P(1)–S(2)–M(1)
S(1)–Pd(1)–S(2)
S(1)–Pd(1)–S(1)#1
S(1)–Pd(1)–S(2)#1
S(1)–P(1)–S(2)
O(1)–P(1)–S(1)
75.176(15)
102.174(17)
115.776(17)
109.903(18)
114.700(18)
125.231(17)
82.49(2)
76.503(15)
100.45(2)
119.137(16)
112.20(2)
119.137(16)
124.399(15)
82.99(2)
84.96(2)
84.76(2)
84.437(18)
180.0
95.563(18)
103.20(3)
114.56(7)
112.68(6)
Fig. 1. Molecular structure of [FcP(OMe)S2Ag(PPh3)2], 1,
88.41(2)
86.62(2)
with hydrogen atoms omitted for clarity.
various metals [3, 5, 8]. Reaction of [Ag(PPh3)2NO3]
with in situ-prepared Na[FcP(OR)S2] in THF afforded
a clear orange solution from which an orange crys-
talline solid of [FcP(OR)S2Ag(PPh3)2] (R = Me 1,
n-Pr 2) was isolated. Complexes 1 and 2 were sta-
ble both as solid and in solution. Two 31P signals at
δ(P) = 43.2 and 111.3 ppm for 1 can be assigned
to the [Ag(PPh3)2]+ and [FcP(OMe)S2]− units, re-
spectively. Similarly, two single peaks at δ(P) = 41.7
and 109.2 ppm in the 31P NMR spectrum of 2 may be
ascribed to the two types of phosphorus atoms with dif-
ferent coordination environments. The 1H NMR spec-
tra of 1 and 2 confirmed the presence of the ferro-
cenyl moieties and the corresponding alkoxides. The
IR spectra of the two complexes clearly showed two
sets of strong bands at ca. 1187 and 1025, and 635
and 576 cm−1 which may be attributed to ν(P – O –
C) and ν(P – S) absorptions, respectively. The three
strong peaks in the range of 480– 530 cm−1 for the
ν(P – C) stretching vibrations indicated the presence of
PPh3 in the two complexes. Mass spectrometry showed
the expected three ions [M]+, [M–PPh3]+ and [M–
2PPh3]+ with the characteristic isotopic distribution
patterns.
113.14(3)
112.75(7)
110.10(7)
113.52(3)
113.62(7)
109.18(7)
O(1)–P(1)–S(2)
a
Symmetry operation: #1 −x, −y+2, −z.
Crystal structure determination
Single crystals of 1 (0.29 × 0.22 × 0.20 mm3), 2 (0.55 ×
0.45 × 0.38 mm3) and 3 (0.26 × 0.19 × 0.12 mm3) were
mounted in random orientation on glass fibers. Diffraction
data were collected on a Bruker SMART Apex CCD diffrac-
˚
tometer with MoKα radiation (λ = 0.71073 A) at 296 K using
an ω scan mode. The collected frames were processed with
the software SAINT [13]. The data were corrected for absorp-
tion using the program SADABS [14]. Structures were solved
by Direct Methods and refined by full-matrix least-squares
on F2 using the SHELXTL software package [15]. All non-
hydrogen atoms were refined anisotropically. The positions
of all hydrogen atoms were generated geometrically (Csp3
–
˚
H = 0.96 and Csp2 – H = 0.93 A) and included in the structure
factor calculations with assigned isotropic displacement pa-
rameters, but were not refined. Crystal data, data collection
parameters and details of the structure refinement are given
in Table 1.
CCDC 749601, 749602, and 749603 contain the supple-
mentary crystallographic data for this paper. These data can
be obtained free of charge from The Cambridge Crystallo-
graphic Data Centre via www.ccdc.cam.ac.uk/data request/
cif.
The structures of the complexes 1 and 2 were de-
termined by room-temperature single-crystal X-ray
diffraction. The results are shown in Figs. 1 and 2,
respectively. Selected bond lengths and angles are
compiled in Table 2 for comparison. Complex 1
crystallizes in the monoclinic space group P21/c
Results and Discussion
The cleavage reaction of dimeric [FcP(S)(µ-S)]2 with four neutral molecules in the cell, while com-
¯
with sodium alkoxide is known to give stable phos- plex 2 crystallizes in the triclinic space group P1
phonodithiolate salts Na[FcP(OR)S2] for ligation to with two neutral molecules in the cell. The silver
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X.-Y. Wang et al. · Silver(I) and Palladium(II) Complexes with Ferrocenyl-phosphonodithiolate Ligands
35
Fig. 3. Molecular structure of [FcP(OMe)S2]2Pd, 3, with hy-
drogen atoms omitted for clarity.
tuted complex [{FcP(OMe)S2}2Pd] (3) as an orange
solid in a yield of 56 %. A similar square-planar pal-
ladium(II) complex [{FcP(OEt)S2}2Pd] has been pre-
viously reported by Woollins and coworkers [5]. The
31P NMR spectrum displayed a sharp singlet at δ(P) =
1
119.5 ppm whilst the H NMR spectrum was as ex-
Fig. 2. Molecular structure of [FcP(OnPr)S2Ag(PPh3)2], 2,
pected confirming the presence of both the ferrocenyl
and ethoxy moieties. The IR spectrum of 3 shows dis-
tinct bands at 1189 and 1027, 634 and 574 cm−1 corre-
sponding to ν(P – O – C) and ν(P – S) absorptions, re-
spectively. The mass spectrum of 3 shows the molec-
ular ion as [M+] at m/z = 728. The structure of 3 is
shown in Fig. 3, and selected bond lengths and angles
are given in Table 2. The central palladium atom re-
sides on a crystallographic inversion center and is co-
ordinated by four sulfur atoms of the [FcP(OMe)S2]−
ligand, forming symmetric PdS2P rings in a square-
planar geometry. The ferrocenyl groups of the two
bound ligands are in a trans arrangement. In 3, the av-
with hydrogen atoms omitted for clarity.
atoms in both complexes are in a tetrahedral geo-
metry with some angle distortions, namely the nar-
row S(1) – Ag(1)– S(2) angles of 75.176(15)◦ for 1
and 76.503(15)◦ for 2 and wide P(2)– Ag(1)– P(3) an-
gles of 125.231(17)◦ for 1 and 124.399(15)◦ for 2,
and are coordinated by the two sulfur atoms of one
S,S-bidentate ligand. The four-membered AgS2P rings
are non-planar and distorted. Each ring contains a
pair of long and short Ag – S bonds [Ag(1)– S(1) =
˚
˚
˚
2.8298(5) A (“long”) and Ag(1)– S(2) = 2.6056(5) A
(“short”) for 1, and Ag(1)– S(1) = 2.7574(6) A
(“long”) and Ag(1)– S(2) = 2.6061(5) A (“short”)
˚
˚
erage Pd – S bond length is 2.3462(6) A, and the bite
angle S – Pd – S is 84.437(18)◦, which agrees well with
for 2]. The average Ag – S bond lengths in 1 (av.
˚
˚
2.7177(5) A) and 2 (av. 2.6818(5) A) are compara-
those in the similar complex [{FcP(OEt)S2}2Pd] [av.
◦
˚
ble to those found in other tetrahedral complexes such
2.355(3) A, 84.211(10) ] [5]. The P – S bond lengths
are almost equal and indicative of multiple bonding
˚
˚
as [Ag(PPh3)2{S2P(Oi-Pr)2}] (2.654(2)– 2.683(2) A)
˚
[16], [Ag(PPh3)2(S2COEt)] (2.549(4)– 2.806(4) A)
[2.0100(7) and 2.0135(7) A], as expected for a delo-
[17], and [Ag(PPh3)2{Fc(S2CNEt2)2}]OTf (OTf = tri-
calized system. A relatively short transannular Pd ··· P
˚
˚
flate, CF3SO3) (2.6047(6)– 2.7025(6) A) [18]. The av-
distance is observed in 3 (2.9507(2) A), similar to that
˚
˚
erage Ag – P bond lengths of 2.4745(5) A in 1 and
found in [{FcP(OEt)S2}2Pd] (2.9501(3) A) [5].
˚
˚
2.4619(4) A in 2 are similar to that of 2.4690(6) A
in [Ag(PPh3)2{Fc(S2CNEt2)2}]OTf [18], but slightly
longer than those in some mononuclear silver(I)-PPh3
complexes with tetra-coordinate silver centers such as
In summary, three silver(I) and palladium(II)
complexes with ferrocenylphosphonodithiolate lig-
ands have been prepared and characterized. The
crystal structures of the three complexes indi-
cate that the S,S-bidentate [FcP(OMe)S2]− an-
ion acts as a chelating ligand for the metal
atoms rather than as a bridging ligand. The reac-
tions of [Ag(PPh3)2]NO3 with [FcP(OR)S2]− gave
1 : 1 products [FcP(OR)S2Ag(PPh3)2] (R = Me 1,
n-Pr 2), whereas the reaction of [Pd(MeCN)2Cl2]
i
˚
[Ag(PPh3)2{S2P(O Pr)2}] (av. 2.449(1) A) [16] and
˚
[Ag(PPh3)2(S2COEt)] (av. 2.441(1) A) [17]. The two
P – S bonds are nearly equal in length [P(1)–S(1) =
˚
1.9843(7) and P(1)–S(2) = 1.9940(7) A for 1, and
˚
P(1)–S(1) = 1.9742(7) and P(1)–S(2) = 1.9986(6) A
for 2] and have a partial π character.
Treatment of [Pd(MeCN)2Cl2] with in situ-prepared with [FcP(OR)S2]− resulted in a 1 : 2 product
Na[FcP(OMe)S2] in MeCN/MeOH gave the substi- [{FcP(OMe)S2}2Pd] (3). Thus, this work clearly
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36
X.-Y. Wang et al. · Silver(I) and Palladium(II) Complexes with Ferrocenyl-phosphonodithiolate Ligands
demonstrates the coordination behavior of ferrocenyl- Acknowledgement
phosphonodithiolates as S,S-bidentate ligands towards
This work was supported by the National Basic Research
transition metal ions. More coordination reactions in-
volving functional [FcP(OR)S2]− ligands are in active
study in this laboratory.
Program of China (973 Program, 2008CB617605) and the
Program for New Century Excellent Talents in University of
China (NCET-06-0556).
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