Synthesis, spectroscopy and structures of palladium(II) and platinum(II) complexes containing mercapto-o-carborane

Article abstract of DOI:10.1016/j.jorganchem.2009.09.014

The reactions of [M₂Cl₂(μ-Cl)₂(PMe₂Ph)₂] with mercapto-o-carboranes in the presence of pyridine afforded mono-nuclear complexes of composition, [MCl(SCb°R)(py)(PMe₂Ph)] (M = Pd or Pt; Cb° =

Full text of DOI:10.1016/j.jorganchem.2009.09.014

Journal of Organometallic Chemistry 694 (2009) 4146–4151
Contents lists available at ScienceDirect
Journal of Organometallic Chemistry
journal homepage: www.elsevier.com/locate/jorganchem
Synthesis, spectroscopy and structures of palladium(II) and platinum(II)
complexes containing mercapto-o-carborane
a
b
b
Nisha P. Kushwah a, Vimal K. Jain a, , Amey Wadawale , Olga B. Zhidkova , Zoya A. Starikova ,
*
Vladimir I. Bregadze b,
*
a Chemistry Divison, Bhabha Atomic Research Center, Mumbai 400 085, India
b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str. 119991, Moscow, Russia
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 18 March 2009
Received in revised form 26 August 2009
Accepted 3 September 2009
Available online 11 September 2009
The reactions of [M2Cl2(l-Cl)2(PMe2Ph)2] with mercapto-o-carboranes in the presence of pyridine affor-
ded mono-nuclear complexes of composition, [MCl(SCb°R)(py)(PMe2Ph)] (M = Pd or Pt; Cb° = o-C2B10H10
;
R = H or Ph). The treatment of [PdCl2(PEt3)2] with PhCb°SH yielded trans-[Pd(SCb°Ph)2(PEt3)2] (4) which
when left in solution in the presence of pyridine gave another substitution product, [Pd(SCb°Ph)2(py)
(PEt3)] (5). The structures of [PdCl(SCb°Ph)(py)(PMe2Ph)] (1), [Pd(SCb°Ph)2(PEt3)2] (4) and [Pd(SCboPh)2
(py)(PEt3)] (5) were established unambiguously by X-ray crystallography. The palladium atom in these
complexes adopts a distorted square-planar configuration with neutral donor atoms occupying the trans
positions. Thermolysis of [PdCl(SCb°)(py)(PMe2Ph)] (2) in TOPO (trioctylphosphine oxide) at 200 °C gave
nanocrystals of TOPO capped Pd4S which were characterized by XRD pattern and SEM.
Ó 2009 Elsevier B.V. All rights reserved.
Keywords:
Mercapto-o-carborane
Palladium
Platinum
Complexes
Synthesis
X-ray
1. Introduction
rane and mercapto-o-carborane with palladium and platinum
complexes and evaluated the suitability of one representative com-
Palladium and platinum chalcogenolate complexes have at-
tracted considerable attention for quite sometime owing to their
diverse structural features [1–4], photo-physical properties [5]
and applications in catalysis [6,7] and materials science [8,9]. Sim-
ple chalcogenolates usually afford polymeric insoluble complexes
limiting their utility as molecular precursors. To suppress polymer-
ization a number of strategies have been adopted. These include
use of ancillary ligands on metal [10,11], internal functionalization
of organochalcogen ligand [12] and sterically demanding ligand
[2,13,14]. The latter strategy suffers from the excessive presence
of carbon which may get incorporated in metal chalcogenide. Thus
ligands containing trimethylsilyl fragments were developed
[15,16]. Another interesting families of ligands incorporating o-car-
boranes may be conceived which would not only impose a three
dimensional steric demand but also give cleaner depositions due
to a weaker C–S linkage. Such ligands, e.g., 1-mercapto-2-phenyl-
o-carborane [17,18], have been known in the literature for quite
some time now [19,20]. Thus in pursuance of our interest on palla-
dium and platinum complexes with organochalcogenolates, we
have examined a few reactions of 1-mercapto-2-phenyl-o-carbo-
pound for the preparation of palladium sulfide nanocrystals. The
results of this work are reported herein.
2. Experimental
All experiments were carried out under anhydrous conditions in
an inert atmosphere. 1H and 31P{1H} NMR spectra were recorded
on a Bruker Avance-II 300 MHz NMR spectrometer. X-ray powder
diffraction data were collected on a Philips X-ray diffractometer
(Model PW 1729) using Cu Ka radiation. SEM (scanning electron
microscopy) and EDAX (energy dispersive X-ray analysis) mea-
surements were made on a MIRERO AIS-2100 and OXFORD INCA
E-350 instrument, respectively. The compounds 1-mercapto-o-car-
borane (Cb°SH) [19], 1-mercapto-2-phenyl-o-carborane (PhCb°SH)
[17,18], [M2Cl2(l-Cl)2(PMe2Ph)2] [21] and [PdCl2(PEt3)2] were pre-
pared according to the literature methods.
2.1. [PdCl(SCb°Ph)(py)(PMe2Ph)] (1)
To a stirred dichloromethane solution of [Pd2Cl2(l-Cl)2(PMe2Ph)2]
(57 mg, 0.09 mmol), PhCb°SH (45 mg, 0.18 mmol) and three drops
of pyridine were added and the whole was stirred for additional
4 h. Addition of diethylether led to precipitation of pyꢀHCl which
was filtered off and the filtrate was concentrated in vacuo. The
* Corresponding authors. Tel.: +70 95 1357 405; fax: +70 951 355 085 (V.I.
Bregadze).
E-mail addresses: janvk@barc.gov.in (V.K. Jain), bre@ineos.ac.ru (V.I. Bregadze).
0022-328X/$ - see front matter Ó 2009 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2009.09.014

N.P. Kushwah et al. / Journal of Organometallic Chemistry 694 (2009) 4146–4151
4147
residue was recrystallized from CH2Cl2–Et2O in 62% yield; m.p.
2.4. [Pd(SCb°Ph)2(PEt3)2] (4)
127 °C (decomp.). Anal. Calcd. for C21H31B10ClNPSPd: C, 41.3; H,
5.1; N, 2.3; Cl, 5.8%. Found: C, 41.4; H, 4.8; N, 2.3; Cl, 6.2%. 1H NMR
in CDCl3: 1.70 (d, 12.0 Hz, PMe); 7.31–7.79 (10H, Ph); 8.76 (br, py):
31P{1H} NMR in CDCl3 d: 5.4 ppm.
Prepared similar to 1 using [PdCl2(PEt3)2] (58 mg, 0.14 mmol)
and PhCb°SH (49 mg, 0.20 mmol) in 30% yield, m.p. 145 °C (de-
comp.). Anal. Calcd. for C28H60B20P2S2Pd: C, 39.8; H, 7.1%. Found:
C, 39.0; H, 7.2%. 1H NMR in CDCl3: 0.87 (q, 8.0 Hz, –CH2); 1.55 (t,
4 Hz, –CH3); 7.3–7.7 (5H, Ph); 31P{1H} NMR in CDCl3 d: 4.3.ppm.
When a dichloromethane solution of 4 containing a few drops
of pyridine was left for several hours a substitution complex,
[Pd(SCb°Ph)2(py)(PEt3)] (5) was isolated, m.p., 95 °C. Anal. Calcd.
for C27H50B20NPS2Pd: C, 40.2; H, 6.2; N, 1.7%. Found: C, 40.6; H,
5.8; N, 1.8%. 1H NMR in CDCl3: 0.95 (m, PCH2CH3), 1.69 (m,
PCH2), 7.33–7.49 (m, Ph + py);, 8.72 (d, 5.2 Hz, py); 31P{1H} NMR
in CDCl3 d: 28.7 ppm.
2.2. [PdCl(SCb°)(py)(PMe2Ph)] (2)
Prepared similar to 1 using [Pd2Cl2(l-Cl)2(PMe2Ph)2] (112 mg,
0.18 mmol) and CboSH (62 mg, 0.35 mmol) in 74% yield, m.p.,
47 °C. Anal. Calcd. for C15H27B10ClNPSPd: C, 33.7; H, 5.1; N, 2.6%.
Found: C, 32.9; H, 4.3; N, 2.6%. 1H NMR in CDCl3: 1.90 (d,
11.6 Hz, PMe); 7.50–7.81 (5H, Ph); 8.97 (m, py). 31P{1H} NMR in
CDCl3 d: 4.7 ppm.
2.5. Thermolysis of [PdCl(SCbo)(py)(PMe2Ph)] (2)
2.3. [PtCl(SCb°Ph)(py)(PMe2Ph)] (3)
TOPO (trioctylphosphine oxide) (2.5 g) was heated in a three
Prepared similar to 1 using [Pt2Cl2(l-Cl)2(PMe2Ph)2] (70 mg,
necked flask up to 200 °C under a nitrogen atmosphere. To this
0.09 mmol) and PhCb°SH (44 mg, 0.17 mmol) in 55% yield, m.p.,
85 °C. Anal. Calcd. for C21H31B10ClNPSPt: C, 36.1; H, 4.5; N, 2.0%.
Found: C, 35.1; H, 3.7; N, 2.4%. 1H NMR in CDCl3 : 1.63 (s, PMe)
7.24–7.93 (10H, Ph), 8.75–8.91 (5H, py). 31P{1H} NMR in CDCl3 d:
ꢁ21.3 (1J(195Pt–31P) = 3506 Hz) ppm.
hot stirring liquid, a dichloromethane (2 ml) solution of 2
(116 mg) was injected using a syringe. The whole was kept at
200 °C with stirring for 3 h. After cooling to room temperature,
the contents were centrifuged leaving a black residue which was
washed with methanol (10 ml ꢂ 3) and dried in vacuo.
Table 1
Crystallographic and structure refinement data for [PdCl(SCb°Ph)(py)(PMe2Ph)] 0.2(C3H6O) (1a), [Pd(SCb°Ph)2(PEt3)2] (4) and [Pd(SCb°Ph)2(py)(PEt3)] (5).
Complex
1a
4
5
Chemical formula
Formula wt.
Color
C21H31B10Cl1N1P1Pd1S1
610.37
Yellow
C28H60B20P2Pd1S2
845.32
Red
C27H50B20N1P1Pd1S2
806.23
Yellow
Crystal size (mm3)
Crystal system
Space group
Unit cell dimensions
a (Å)
0.45 ꢂ 0.35 ꢂ 0.20
Monoclinic
P21/c
0.40 ꢂ 0.35 ꢂ 0.20
Monoclinic
C2/c
0.1 ꢂ 0.4 ꢂ 0.4
Monoclinic
P21/n
17.326(2)
10.773(1)
16.136(2)
100.543(2)
2820.3(5)
4
13.926(9)
16.158(1)
19.972(1)
102.440(1)
4388.7(5)
4
22.000(6)
11.826(6)
18.420(6)
101.03(2)
4704(3)
4
b (Å)
c (Å)
b (°)
V (Å3)
Z
Dcalc (g cmꢁ3
)
1.438
1.280
1.139
Diffractometer
T, K
Bruker SMART
120
Bruker APEX 2
100
Rigaku AFC7S
298
2hmax (°)
Absolute coefficient,
54
5.61
54
6.14
55
0.538
l
(Mo K
a
) (cmꢁ1
)
Absorption correction
Tmax and Tmin
No. of reflections collected
No. of unique reflections collected (Rint
No. of observed reflection (I > 2
SADABS
SADABS
Psi-scans
0.900 and 0.8135
12 978
10 884 (0.0587)
6534
0.695 and 0.561
25 293
6073 (0.0522)
2327
0.658 and 0.730
24 428
4860 (0.0307)
2284
)
r(I))
No. of parameters
327
294
469
R1 (on F for obs. reflections)
wR2 (on F2 for all reflection)
GOF
0.482
0.1083
1.077
0.126 and ꢁ0.523
0.0230
0.0620
1.014
0.055 and 0.337
0.590
0.1218
1.060
1.0300 and ꢁ0.7800
Largest difference peak and hole (e Åꢁ3
)
R
S
R
SH
Me2PhP
Cl
Py
C
M
M2Cl2(μ-Cl)2(PMe2Ph)2
+
Py
BH
1 - 3
M=Pd, Pt; R=H, Ph
Scheme 1.

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N.P. Kushwah et al. / Journal of Organometallic Chemistry 694 (2009) 4146–4151
2.6. Crystallography experiment
onances. The 31P{1H} NMR spectra showed a single resonance sug-
gesting the formation of only one isomeric species.
Single-crystal X-ray diffraction experiments were carried on
Bruker SMART 1000 CCD, Bruker APEX 2 and Rigaku AFC7S diffrac-
tometers for 1, 4 and 5, respectively, using graphite monochromat-
ed Mo K radiation (k = 0.71073 Å). Low temperature of the crystals
was maintained with a Cryostream (Oxford Cryo-systems) open-
flow N2 gas cryostat. Reflection intensities were integrated using
SAINT software and semi-empirical method SADABS [22,23]. The struc-
tures were solved by direct methods [24], and refinement was on
F2 [25] using data corrected for absorption correction effects with
an empirical procedure [26,27]. The non-hydrogen atoms were re-
fined with anisotropic displacement parameters. All carborane
hydrogen atoms in 1a and 4 were located from the difference Fou-
rier syntheses, the H(C) atoms were placed in geometrically calcu-
lated positions. All hydrogen carbon atom positions in 1a and 4 and
carborane hydrogen atom positions in 1a were refined in isotropic
approximation using riding model with the Uiso(H) parameters
equal to 1.2 Ueq(Xi) or Ueq(Ci), where U(Xi) are the equivalent ther-
mal parameters of the boron and methyne carbon. The carborane
hydrogen atom positions for 4 were refined in isotropic approxi-
mation. All hydrogen atoms in 5 were placed in calculated posi-
tions and refined in isotropic approximation using riding model.
All calculations were performed on an IBM PC/AT using the SHELXTL
software [25]. Molecular structure was drawn using ORTEP [28].
Crystallographic data and structural refinement details are given
in Table 1.
A freshly prepared CDCl3 solution of the platinum complex (3)
exhibited a single resonance with 1J(Pt–P) of 3506 Hz. The complex
slowly isomerized in solution to another species in which phos-
phine is trans to pyridyl nitrogen (d 31P: ꢁ20.4 (1J(Pt–
P) = 3528 Hz). The two species existed in 1:1 ratio (Scheme 2).
100
80
60
40
20
0
0
10
20
30
40
50
60
70
80
2θ
3. Results and discussion
Fig. 1. XRD pattern of Pd4S obtained from thermolysis of [PdCl(SCb°)(py)(PMe2Ph)]
(2) in TOPO at 200 °C.
Treatment of [M2Cl2(
lents of mercapto-o-carboranes in the presence of pyridine as
HCl scavenger afforded mono-nuclear complexes,
[MCl(SCb°R)(py)(PMe2Ph)] (M = Pd or Pt; R = H or Ph) rather than
l-Cl)2(PMe2Ph)2] with two mole equiva-
the expected thiolato-bridged binuclear derivatives, [M2Cl2(
l
-
SCb°R)2(PMe2Ph)2] (Scheme 1).
It is noteworthy that the binuclear complexes [M2Cl2(
l
-
SR)2(PMe2Ph)2] (M = Pd or Pt) are inert to bridge cleavage reactions
by ligands like pyridine [29]. The steric bulk of carborane in the
present case seems to facilitate the formation of mono-nuclear
products which are interesting examples of square-planar com-
plexes containing four different ligands. In the 1H NMR spectra of
these complexes the SH proton resonance was absent indicative
of deprotonation of the ligand. The spectra exhibited expected res-
SCboPh
py
SCboPh
Cl
PMe2Ph
Cl
PMe2Ph
py
Pt
Pt
Fig. 2. SEM micrograph of Pd4S obtained from thermolysis of [PdCl(SCb°)(py)
(PMe2Ph)] (2) in TOPO at 200 °C.
Scheme 2.
Ph
Ph
Ph
SH
S
Et3P
8h, 20oC
Py
S
Et3P
Py, 20oC
Pd
PdCl2 (PEt3)2
2
+
Pd
S
PEt
3
S
Py
C
Ph
BH
Ph
4
5
Scheme 3.

N.P. Kushwah et al. / Journal of Organometallic Chemistry 694 (2009) 4146–4151
4149
Reaction of [PdCl2(PEt3)2] with PhCb°SH in the presence of pyr-
idine yielded initially trans-[Pd(SCb°Ph)2(PEt3)2] (4) (d 31P:
4.3 ppm). When the solution was left for several hours at room
temperature, yellow crystals of [Pd(SCb°Ph)2(py)(PEt3)] (5) were
formed by substitution of one triethyl phosphine ligand by pyri-
dine. It is rather unusual in a sense the strong binding phosphine
ligand is replaced by pyridine (Scheme 3).
To access the suitability of these complexes for the prepara-
tion palladium sulfide nanocrystals, thermolysis of one represen-
tative complex 2 was carried out in TOPO (trioctylphosphine
oxide). The complex 2 on thermolysis at 200 °C gave a black res-
idue of TOPO capped Pd4S as revealed by EDAX (Calcd for Pd4S:
Pd, 93.0; S, 7.0; Found: Pd, 92.2; S, 4.7; P, 1.15%) and XRD pat-
tern (Fig. 1) (JCPDS File No 10-335). The SEM micrograph (Fig. 2)
showed that the particles are spherical in shape with an average
diameter of ꢃ100 nm. Extrusion of carborane in metal complexes
has been reported recently to give metal nanoparticles [30]. For
example, the complex [IrH(7,8-nido-C2B9H11)(PPh3)2] in ethylene
glycol under hydrogen atmosphere at 160 °C yields iridium
nanoparticles [30].
Table 2
The selected bond lengths (Å) and angles (°) for 1, 4 and 5.
[PdCl(SCb°Ph)(py)(PMe2Ph)] (1)
[Pd(SCb°Ph)2(PEt3)2] (4)
[Pd(SCb°Ph)2(py)(PEt3)] (5)
Pd–S
Pd–P
Pd–Cl
Pd–N
2.302(1)
2.243(1)
2.342(1)
2.141(3)
0.059
2.3595(4)
2.3582(4)
2.3168(15), 2.3380(16)
2.2564(16)
2.117(5)
D
Pd (Å)
0.212
S–C1(cb)
1.781(4)
1.759(6)
1.499(5)
1.719(6)
1.709(6)
1.698(6)
1.741(6)
1.738(6)
1.724(6)
1.715(6)
1.719(6)
1.768(1)
1.777(2)
1.503(2)
1.731(2)
1.710(2)
1.706(2)
1.737(2)
1.733(2)
1.720(2)
1.701(2)
1.703(2)
1.763(6), 1.795(6)
1.751(8), 1.741(8)
1.510(9), 1.500(8)
1.728(9)
1.720(9)
1.725(9)
1.744(9)
1.719(10)
1.726(9)
1.672(10)
C1(cb)–C2(cb)
C2(cb)–C(Ph)
C1(cb)–B(3)
C1(cb)–B(4)
C1(cb)–B(5)
C1(cb)–B(6)
C2(cb)–B(3)
C2(cb)–B(6)
C2(cb)–B(7)
C2(cb)–B(11)
1.711(9)
1
4
5
S–Pd–Cl
S–Pd–P
S–Pd–N
Cl–Pd–N
N–Pd–P
177.41(4)
90.41(4)
90.92(10)
88.19(10)
176.19(9)
S–Pd–S0
P–Pd–P10
P–Pd–S
179.62(2)
158.91(2)
89.16(1)
S1–Pd–S2
S1–Pd–P
S2–Pd–P
N–Pd–S1
N–Pd–S2
N–Pd–P
177.000(5)
91.26(6)
86.00(6)
91.25(13)
91.54 (14)
176.20(15)
Fig. 3. (a) Molecular structure of [PdCl(SCb°Ph)(py)(PMe2Ph)] (1) drawn with 50% probability; (b) Inter- and intra-molecular hydrogen bond in 1a (the distances
Cl(1)ꢀ ꢀ ꢀH(9c), Cl(1)ꢀ ꢀ ꢀH(12a) and Cl(1)ꢀ ꢀ ꢀH(9aa) 2.71, 2.75, and 2.64 Å, respectively, the bond angles Cl(1)–H–C equal to 117°, 145° and 156°, respectively).

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N.P. Kushwah et al. / Journal of Organometallic Chemistry 694 (2009) 4146–4151
strong trans influence of the phosphine in the latter. The C–S dis-
tances in all these complexes vary between 1.763(6) and 1.795
(6) Å, which can be compared with those reported in Cb°–SH
(1.776 Å) and Cb°–SPh (1.784 Å) [32,33]. The C–C bond length in
carboranes is sensitive to the nature of attached sulfur atom. The
C–C distances in Cb°–SH, Cb°–SPh and Cb°–Sꢁ are 1.720, 1.708
and 1.836 Å, respectively [32–34]. The C–C distances in our com-
plexes lie in the range 1.741(8)–1.777(2) Å which are slightly
shorter than the one reported in Cb°–Sꢁ anion.
The steric demand of three dimensional carborane fragment is
reflected on various angles around palladium atom. The P–Pd–P
angle in 4 has been reduced significantly (158.91°) from the ideal
value of 180°. When one of the phosphines is replaced by a less
bulky pyridine ligand as in 1 and 5, the P–Pd–N (angles involving
neutral donors) is opened up (ꢃ176°). The angles S–Pd–E (E = Cl
or S) (177.0–179.6°) are closed to ideal value of 180°.
4. Molecular structures of [PdCl(SCb°Ph)(py)(PMe2Ph)] (1),
[Pd(SCb°Ph)2(PEt3)2] (4) and [Pd(SCb°Ph)2(py)(PEt3)] (5)
Molecular structures of 1, 4 and 5 have been established unam-
biguously by X-ray crystallography. Selected bond lengths and an-
gles are given in Table 2 and ORTEP drawings with crystallographic
numbering schemes are shown in Figs. 3–5. The palladium atoms
in these complexes adopt a distorted square-planar configuration
defined by ‘‘ClNPS”, ‘‘S2P2” and S2NP” donor sets in 1, 4 and 5,
respectively. The neutral donors in these complexes occupy mutu-
ally trans positions.
Trans influence of various donor atoms around palladium was
reflected in their bond distances involving palladium atom. Thus
Pd–S distance in 1 is slightly shorter than those observed in 4
and 5, due to weak trans influence of the chloride ion, although
the Pd–S distances in all these complexes are within the range re-
ported for palladium thiolates [9,11,31]. Similarly the Pd–P dis-
tances in 1 and 5 are shorter by ꢃ0.1 Å than 4 owing to the
In 1 there are weak interaction between Cl and one of the
hydrogen atoms of the methyl group of PMe2Ph (Fig. 1b) as Clꢀ ꢀ ꢀH
Fig. 4. (a) Molecular structure of [Pd(SCb°Ph)2(PEt3)2] (4) drawn with 50% probability; (b) intra-molecular interactions between Pd atom and hydrogen atoms of carborane in
4.
Fig. 5. Molecular structure of [Pd(SCb°Ph)2(py)(PEt3)] (5) drawn with 50% probability.

N.P. Kushwah et al. / Journal of Organometallic Chemistry 694 (2009) 4146–4151
4151
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Acknowledgements
The authors are thankful to the Department of Science and
Technology (DST), New Delhi and Russian Academy of Sciences,
Moscow for financial support under ILTP Project No. B-5.22. One
of authors Zoya A. Starikova thanks the Russian Foundation for Ba-
sic Research (Project 07-03-00631) and Grant NSh-3019.2008.3 for
financial support.
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Appendix A. Supplementary data
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CCDC 701528, 701529 and 713153 contain the supplementary
crystallographic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic Data Centre
via www.ccdc.cam.ac.uk/data_request/cif. Supplementary data
associated with this article can be found, in the online version, at
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