Spectroscopic analysis and molecular structures of mononuclear bis(t-butyltrithiocarbonato)-nickel, -palladium and (t-butyltrithiocarbonato)(t-butylthiolato)platinum dimer

Article abstract of DOI:10.1016/j.ica.2021.120382

Treatment of the bis(triphenylphosphine)dichlorometal (PPh₃)₂MCl₂ (M = Ni, Pd, Pt) with the trithiocarbonato anion (Bu^tSCS₂^-) gave products depending on the metal center. In case of nickel, the product is Ni(κ²S,S-S₂CSBu^t)₂ (1) while for the palladium case, a similar complex Pd(κ²S,S-S₂CSBu^t)₂ (2) was obtained in addition to the dithiocarbonato complex (PPh₃)₂Pd(κ²S,S-S₂C = O). However, the platinum reaction gave two products, a dimeric species Pt₂(μ-SBu^t)₂(κ²S,S-S₂CSBu^t)₂ (3) and the known trithiocarbonato complex (PPh₃)₂Pt(κ²S,S-S₂C = S). These products were characterized by IR, ¹H, ¹³C{¹H} NMR and UV–Vis spectroscopy. Crystal structures of these complexes were determined by single crystal X-ray diffraction measurements.

Full text of DOI:10.1016/j.ica.2021.120382

Inorganica Chimica Acta 522 (2021) 120382
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Research paper
Spectroscopic analysis and molecular structures of mononuclear bis
(t-butyltrithiocarbonato)-nickel, -palladium and (t-butyltrithiocarbonato)
(t-butylthiolato)platinum dimer
,
Mohammad El-khateeba *, Hayato Moriyamab, Yukihiro Yoshidab, Hiroshi Kitagawab
a Chemistry Department, Jordan University of Science and Technology, Irbid 22110, Jordan
b Division of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-Oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan
A R T I C L E I N F O
A B S T R A C T
Keywords:
Treatment of the bis(triphenylphosphine)dichlorometal (PPh3)2MCl2 (M = Ni, Pd, Pt) with the trithiocarbonato
anion (ButSCS2- ) gave products depending on the metal center. In case of nickel, the product is Ni(κ2S,S-S2CSBut)2
(1) while for the palladium case, a similar complex Pd(κ2S,S-S2CSBut)2 (2) was obtained in addition to the
dithiocarbonato complex (PPh3)2Pd(κ2S,S-S2C = O). However, the platinum reaction gave two products, a
dimeric species Pt2(µ-SBut)2(κ2S,S-S2CSBut)2 (3) and the known trithiocarbonato complex (PPh3)2Pt(κ2S,S-S2C =
S). These products were characterized by IR, 1H, 13C{1H} NMR and UV–Vis spectroscopy. Crystal structures of
these complexes were determined by single crystal X-ray diffraction measurements.
Nickel
Palladium
Platinum
t-Butyltrithiocarbonate
X-ray structure
Synthesis
Characterization
1. Introduction
Platinum group metal complexes of dithiocarbamato and dithio-
carbonato ligands are well documented in the literature [22–32].
Dithioacid ligands {dithiocarbamate (R2NCS-2), dithiocarbonate
(ROCS-2) and trithiocarbonate (RSCS-2)} are versatile ligands which can
coordinate to almost all metals of the periodic table [1–3]. The ligands
themselves find many applications such as metal-ore flotation [4],
fungicides, high pressure lubricants, pesticides and accelerators used in
vulcanization [5]. Their metal complexes have attracted intense atten-
tion due to their wide applications including their use as anti-alcoholic
or anticancer drugs and for AIDS treatment [6–10]. They are also used
for biological remediation [11], non-linear optical applications [12],
synthetic precursors for the generation of metal sulfide nanoparticles
[13–15], as well as therapeutic agents [16–21]. Thioplatin; bis(O-eth-
yldithiocarbonato)platinum(II), is found to have antitumor activity
against a number of human tumor lines [17].
However, those of the trithiocarbonates are much less investigated
owing to their instability towards CS2 elimination [33]. Few examples of
homoleptic palladium or nickel complexes with trithiocarbonato ligands
of the general formula M(κ2S,S-S2CSR)2 (M = Ni; R = Et, But, benzyl. M
= Pd; R = But) are known [33–36]. The latter complexes undergo CS2
elimination in solution leading to the trithiocarbonato/thiolato dimers
[M(µ-SR)(κ2S,S-S2CSR)]2. The structure of [Ni(µ-SCH2Ph)(κ2S,S-
S2CSCH2Ph)]2 has a distorted square planar geometry with a non-planar
syn-endo Ni2S2 rhombus while the analogous Pd-complex [Pd(µ-SCMe3)
(κ2S,S-S2CSCMe3)]2 has a similar distorted square planar geometry but
with a non-planar anti Pd2S2 rhombus [36]. These bis(dithioacid) metal
complexes interacted with phosphine, phosphite or bis(phosphine) li-
gands to generate different types of products depending on the nature of
the ligand, the metal center and the reaction conditions [37–41].
The complexes (PPh3)2MCl2 (M = Pd, Pt) reacted with one equiva-
lent of pyrrolidine dithiocarbamato anion to give (PPh3)M(Cl)(κ2S,S-
S2CNC4H8), while using a 1:2 metal to ligand molar ratio gave (PPh3)Pt
(κS-S2CNC4H8)(κ2S,S-S2CNC4H8) [42]. Moreover, (dppe)MCl2 reacted
with the same ligand to give the salts [M(κ2S,S-S2CNC4H8)(κ2P,P-dppe)]
Cl [42].
Recently, gold dithiocarbamato complexes are reported and showed
selective inhibitors of mitochondrial respiration. These compounds
exhibited 50% inhibitory concentration against aggressive cancer types
with significant selectivity for cancer cells over normal cells [20].
However, silver and copper dithiocarbamato complexes supported by
triphenylphosphine demonstrated high activity against all bacterial
strains. Some of these complexes are found to be active agents for
antioxidant activity against DPPH and NO free radical scavengers [21].
The interaction of (PPh3)2MCl2 with trithiocarbonato ligands is
* Corresponding author.
E-mail address: kateeb@just.edu.jo (M. El-khateeb).
https://doi.org/10.1016/j.ica.2021.120382
Received 19 February 2021; Received in revised form 29 March 2021; Accepted 29 March 2021
Available online 1 April 2021
0020-1693/© 2021 Elsevier B.V. All rights reserved.

M. El-khateeb et al.
Inorganica Chimica Acta 522 (2021) 120382
unknown to the best of our knowledge. Therefore, in this paper we
present the reactions of (PPh3)2MCl2 with t-butyltrithiocarbonato anion.
The resulted complexes are fully characterized by spectroscopic tech-
niques. We also present the first structurally characterized monomeric M
(κ2S,S-S2CSBut)2 (M = Ni (1), Pd (2)) complexes in addition to a dimeric
[Pt(µ-SBut)(κ2S,S-S2CSBut)]2 (3) complex.
than the corresponding peaks of the dithiocarbamato complexes (M(κ2S,
S-S2CNR2)2: 200.2–214.6 ppm) [45–48] and also higher than those of
the corresponding peaks of the dithiocarbanoates (Pt(κ2S,S-S2COR)2:
233.3–234.9 ppm) [15,16]. For the dimeric complex 3, four signals
(30.5, 33.5, 49.5, 55.4 ppm) due to the thiolato and trithiocarbonato C-
atoms and a signal at 245.1 ppm for the CS3 were observed.
2. Results and discussion
2.2. Structural features of complexes 1–3
2.1. Synthesis and characterization
Complexes 1 and 2 belong to the monoclinic system with space group
P21/c measured at 100 K (Table 1), and their views, with the atom
numbering schemes, are depicted in Figs. 1 and 2, respectively. Half of
The reactions of the bis(triphenylphosphine)dichloro-nickel, palla-
dium or platinum with the t-butyltrithiocarbonato anion were investi-
gated. The product types were found to depend on the metal center
(Scheme 1). The nickel-reaction produced the bis(t-butyl-
trithiocarbonato)nickel (1) in addition to triphenylphosphine-sulfide
and -oxide as proved by the 31P{1H} NMR spectrum of the reaction
mixture. In case of palladium, two products were also obtained, Pd(κ2S,
S-S2CSBut)2 (2) and the known dithiocarbonato complex (PPh3)2Pd(κ2S,
S-S2C = O) which may be resulted from water hydrolysis of the tri-
thiocarbonato complex [43]. The platinum-reaction gave also two
products namely, Pt2(µ-SBut)2(κ2S,S-S2CSBut)2 (3) and the known tri-
thiocarbonato complex (PPh3)2Pt(κ2S,S-S2C = S) [44].
Table 1
Crystallographic data for 1–3.
1
2
3
CCDC No.
2046729
C10H18NiS6
389.31
2046730
C10H18PdS6
437.00
2046731
C18H36Pt2S8
899.13
Empirical formula
Formula weight (g
molꢀ 1
)
Temperature (K)
Wavelength (Å)
Crystal system
Space group
Unit cell dimensions
a (Å)
100(2)
100(2)
100(2)
0.71073
Monoclinic
P21/c
0.71073
Monoclinic
P21/c
0.71073
Orthorhombic
Pnma
Complexes 1–3 are already known and were obtained by different
methodology which involved the reactions of the trithiocarbonato anion
and the M(II) salts [33]. However, their spectral data and crystal
structures are not reported to date. The structures of 1–3 have been
identified based on their spectroscopic data (IR, 1H NMR, 13C{1H} NMR,
UV–Vis) and X-ray structure determination.
5.84569(18)
13.6629(4)
10.4652(3)
90
5.82131(19)
13.9964(4)
10.4537(3)
90
11.5582(4)
23.2460(7)
10.7119(3)
90
b (Å)
c (Å)
α
(◦)
β (◦)
104.222(3)
90
104.003(3)
90
90
γ (◦)
90
The IR spectra of complexes 1–3 showed two strong bands
(1153–1157, 978–987 cmꢀ 1) due to asymmetric and symmetric car-
bon–sulfur stretching frequencies, respectively. These frequencies are
comparable to those reported for the corresponding dithiocarbamato
and dithiocarbonato analogues (1040–1154, 950–1000 cmꢀ 1) [44–46].
The 1H NMR spectra of complexes 1 and 2 displayed two singlets (1:
1.21, 1.64 ppm, 2: 1.42, 1.69 ppm) due to the presence of two isomers in
solution. The spectrum of 3 showed similar two singlets (1.41, 1.66
ppm) due to the two types of ligands; thiolate and trithiocarbonate. The
13C{1H} NMR spectra of complexes 1 and 2 presented four peaks of t-
butyl carbons for the two isomers (1: 30.3, 33.7, 44.8, 55.4 ppm, 2: 30.1,
33.5, 45.5, 55.8 ppm) as proved by the 1H NMR spectra of these com-
plexes. The spectra also have a peak (1: 244.8 ppm, 2: 244.7 ppm) for
the carbon atom of the trithiocarbonato ligand. These shifts are higher
V (Å3)
810.23(4)
2
826.43(5)
2
2878.09(15)
4
Z
ρcalcd (g cmꢀ 3
)
1.596
1.756
2.075
μ
(mmꢀ 1
)
1.947
1.858
10.296
1712
F(000)
404
440
Crystal size (mm3)
0.25 × 0.15 ×
0.10
0.40 × 0.15 ×
0.10
0.50 × 0.20 ×
0.10
Reflections collected
Independent
10,446
10,796
21,072
3896 [R(int) =
0.0398]
142
2213 [R(int) =
0.0222]
82
2208 [R(int) =
0.0279]
82
reflections
Refined parameters
R
1 [I > 2
σ
(I)]
0.0155
0.0158
0.0195
0.0415
1.042
wR2 (all data)
0.0389
0.0396
Goodness-of-fit on F2
Largest diff. peak and
1.063
1.126
0.35 and ꢀ 0.22
0.45 and ꢀ 0.61
1.18 and ꢀ 1.04
hole (eÅꢀ 3
)
Scheme 1. Reactions of (PPh3)2MCl2 with the trithiocarbonato anion (ButSCS2- ).
2

M. El-khateeb et al.
Inorganica Chimica Acta 522 (2021) 120382
of the van der Waals radii: 3.60 Å (Fig. 3b)) [51].
Complex 3 crystallizes in the orthorhombic system with space group
Pnma measured at 100 K (Table 1). The asymmetric unit contains half
molecule (Fig. 4), and two S atoms (S1 and S2) and two t-butyl groups
(C1–C3 and C4–C6) lie on the mirror planes at z = 0.25 and 0.75. The
molecular structure consists of two platinum trithiocarbonato units
bridged by thiolate groups resulting in the formation of a four-
membered Pt2S2 ring with a Pt–Pt distance of 3.2219(2) Å. The dihe-
dral angle between the two PtS2C planes was estimated to be 120.5◦.
Each platinum center is coordinated to one trithiocarbonato group and
two thiolates, resulting in a four coordinate square planar geometries
with S-Pt-S angles ranging from 74.10(2) to107.07(2)◦. The bridging
thiolates are present in anti-configuration to each other, as shown for the
analogous Pd-species [34]. The average Pt-S(trithiocarbonate) bond
distance (2.3267(4) Å) is comparable to the Pt–S(thiolate) bond length
Fig. 1. Molecular structure of 1 determined by X-ray diffraction, where Ni1 is
in a special position 2d. Symmetry operation (′): 1-x, 1-y, -z.
–
(2.3163(4) Å). The C S bonds within the trithiocarbonato ligand (1.706
–
(2) Å) are shorter than the C S bonds of the bridging thiolates (1.866(3)
Å). Similar results are reported for the corresponding nickel and palla-
dium dimers [34].
As shown in Fig. 5, the void surrounded by a bent molecule accom-
modates a t-butyl group of the adjacent molecule for constructing the
infinite zigzag-arrays along the a axis. The arrays are connected to each
Fig. 2. Molecular structure of 2 determined by X-ray diffraction, where Pd1 is
in a special position 2d. Symmetry operation (′): 2-x, 1-y, 2-z.
–
other through C H⋅⋅⋅S hydrogen bonds between molecules bent in
opposite directions (H11c⋅⋅⋅S4: 2.98 Å vs sum of the van der Waals radii:
the molecule is crystallographically independent, and the central metal
atom is located at an inversion center. Both structures consist of a dis-
torted square planar geometry around the metal center as shown by the
S–M–S angle within the 4-membered ring of 78.766(9)◦ for 1 and 74.792
(12)◦ for 2 leaving the other S–M–S (between the two rings) to expand to
101.234(9)◦ for 1 and 105.208(12)◦ for 2. In both molecules, the central
metal atom is coordinated to two trithiocarbonato ligands in a bidentate
fashion forming the bicyclic [CS2MS2C] moiety as a combination of two
four-membered [MS2C] metallocycles. The average Ni–S (2.2132(2) Å)
and Pd–S (2.3312(3) Å) distances are typical of such values reported for
3.00 Å [51], C11⋅⋅⋅S4: 3.84 Å, C11–H11c⋅⋅⋅S4 angle: 147.1◦).
–
S
dithiocarbonato and dithiocarbamato complexes [45–48]. The C
bond lengths of the trithiocarbonato ligand are very close to each other,
indicating that the double bond is delocalized over the three positions.
Complexes 1 and 2 have isomorphous structures, therefore, only the
structural feature of 1 is described. Within the bc plane, the molecules
construct a slipped sandwich herringbone pattern with a dihedral angle
of ca. 56◦ (Fig. 3a), in which each nickel atom is coordinated by two
methyl groups of adjacent molecules through agostic hydrogen bonds
[49,50] with a Ni⋅⋅⋅H distance of 2.72 Å (a Pd⋅⋅⋅H distance of 2.82 Å for
2). Along the a axis, each of the molecules is arranged uniformly through
short S⋅⋅⋅S heteroatomic contacts (S1⋅⋅⋅S1: 3.39 Å, S1⋅⋅⋅S2: 3.56 Å vs sum
Fig. 4. Molecular structure of 3 determined by X-ray diffraction, where S1, S2,
C1, C3, C4 and C6 are in special positions 4c. Hydrogen atoms are omitted for
clarity. Symmetry operation (′): x, 3/2-y, z.
Fig. 3. Crystal structures of 1 viewed along (a) the a axis (b) the b axis. Blue dotted lines show Ni⋅⋅⋅H agostic hydrogen bonds in (a) and S⋅⋅⋅S heteroatomic contacts
in (b).
3

M. El-khateeb et al.
Inorganica Chimica Acta 522 (2021) 120382
3.3. General procedure for the reactions
The compound (PPh3)2MCl2 (0.25 mmol) was dissolved in 20 mL of
THF. To this solution, three equivalents of the sodium t-butyl-
trithiocarbonate (84 mg, 0.75 mmol) was added and a sudden change in
the color (Ni: brown, Pd: red, Pt: dark red) was observed. The resulting
mixture was stirred at room temperature for 1 hr. The volatiles were
removed under vacuum and the residue was extracted with hexane (3 ×
5 mL). This colored hexane solution was evaporated slowly yielding the
Ni(κ2S,S-S2CSBut)2 (1), Pd(κ2S,S-S2CSBut)2 (2) or Pt2(µ-SBut)2(κ2S,S-
S2CSBut)2 (3). The residue (left after hexane extraction) was crystallized
from CH2Cl2/hexane to give (PPh3)2M(κ2S,S-S2CE) for M = Pd, E = O, M
= Pt, E = S and gave white crystals of S = PPh3 in case of M = Ni.
Ni(κ2S,S-S2CSBut)2 (1). Brown (40 mg, 82%). IR (KBr, cmꢀ 1): 1450,
1365, 1157, 980, 906. 1H NMR (600 MHz, CDCl3): δ 1.21 (s, 9H, CH3);
1.64 (s, 9H, CH3). 13C{1H} NMR (150 MHz, CDCl3): δ 30.3 CH3, 33.7
CH3, 44.8 C(CH3)3, 55.4 C(CH3)3, 240.8 CS3. UV–Vis (CH2Cl2, λmax, nm)
280, 330.
Pd(κ2S,S-S2CSBut)2 (2). Red (41 mg, 75%). IR (KBr, cmꢀ 1): 1452,
1365, 1157, 978, 906. 1H NMR (600 MHz, CDCl3): δ 1.42 (s, 9H, CH3);
1.69 (s, 9H, CH3). 13C{1H} NMR (150 MHz, CDCl3): δ 30.1 CH3, 33.8
CH3, 45.5 C(CH3)3, 55.8 C(CH3)3, 244.7 CS3. UV–Vis (CH2Cl2, λmax, nm)
280, 320, 410.
Pt2(µ-SBut)2(κ2S,S-S2CSBut)2 (3). Dark Red (60 mg, 80%). IR (KBr,
cmꢀ 1): 1450, 1361, 1153, 987, 924. 1H NMR (600 MHz, CDCl3): δ 1.41
(s, 9H, CH3); 1.66 (s, 9H, CH3). 13C{1H} NMR (150 MHz, CDCl3): δ 30.5
CH3, 33.5 CH3, 49.5 C(CH3)3, 55.4 C(CH3)3, 245.1 CS3. UV–Vis (CH2Cl2,
λmax, nm) 280, 330.
Fig. 5. Molecular arrangement of 3, where t-butyl groups (C4–C6) drawn in red
protrude toward the void surrounded by the adjacent molecule. Hydrogen
atoms are omitted for clarity.
2.3. UV–visible spectroscopy of complexes 1–3
3.4. X-ray crystal structure analysis
The electronic spectra of complexes 1–3 were recorded in dichloro-
methane at room temperature. Each of the spectrum of 1 and 2 has three
absorption bands in the ranges of 280 nm, 330, 370 nm and 410, 500
nm. The first two-absorption bands are corresponding to ligand-to-
ligand (LLCT) or metal-to-ligand (MLCT) charge transfer bands and
the third weak excitation is ascribed chiefly to d-d metal transitions,
explaining the big difference from one complex to the other. The spec-
trum of 3 showed also the two-bands at 280 and 330 nm similar to those
of 1 and 2 while, the d-d transition is absent from the spectrum of 3 in
accordance with reported data for Pt complexes [27]. These values and
assignment are similar to those reported for analogous systems [8,27].
Crystals of suitable sizes were mounted on a Rigaku XtaLAB P-200
diffractometer fitted with SHELXTL for structure determination. X-ray
data were collected using Mo K
α radiation (λ = 0.71073 Å). Direct
method using SHELXS-2014 [52] was employed to solve the structure
and Fourier transformation was carried out using SHELXL-2014 [53]
employing full-matrix least square refinement calculations. Hydrogen
–
atoms were geometrically placed under the assumption of a fixed C
H
bond length of 0.98 Å with an sp3 configuration of the parent atoms.
4. Conclusion
In summary, the reaction of (PPh3)2MCl2 with ButSCS2- resulted in
two complexes; one obtained from the substitution of both phosphine
and chloro ligands while the other is resulted from substitution of only
the chloride ligands by the trithiocarbonato anion which later undergo
3. Experimental part
3.1. General
–
C
S bond cleavage producing the trithiocarbonato complex (PPh3)2Pt
Solvents of super-dry quality were used as received. Sodium t-butyl
thiolate, carbon disulfide and the compounds (PPh3)2MCl2 (M = Ni, Pd)
were obtained from Aldrich while (PPh3)2PtCl2 was prepared according
to reported procedures [47].
(κ2S,S-S2C = S), or dithiocarbonato complex (PPh3)2Pd(κ2S,S-S2C = O).
In the case of M = Pt, a dimeric complex is obtained. The metal center in
all complexes is four coordinate in distorted square planar geometry
with small S-Mꢀ S angle.
The NMR spectra were measured with JEOL JNM-ECA 600 MHz
spectrometer. Chemical shifts are given in ppm relative to TMS at 0 ppm
for 1H NMR and relative to external H3PO4 for 31P{1H} NMR. The
Fourier transform infrared (FT-IR) spectra were recorded as a KBr pellet
on a Thermo Nicolet Nexus 670 FT-IR spectrometer. The electronic ab-
sorption spectra were recorded on a JASCO V-570 UV/VIS/NIR
spectrometer
Declaration of Competing Interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence
the work reported in this paper.
Acknowledgement
3.2. Preparation of sodium t-butyltrithiocarbonate
M. El-khateeb thanks Jordan University of Science and Technology
for sabbatical leave (Grant No. 240/2019) and the Arab Fund for Eco-
nomic and Social Development, Kuwait for scholarship.
Sodium t-butyl thiolate (5.60 g, 50 mmol) was dissolved in 100 mL of
THF and cooled to 0˚C. To this solution carbon disulfide (3.02 mL, 50
mmol) was added dropwise. The cooling bath was removed and the
mixture was warmed to room temperature for 3 hrs. The resulting yel-
low solution was used for farther reactions.
4

M. El-khateeb et al.
Inorganica Chimica Acta 522 (2021) 120382
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Appendix A. Supplementary data
[23] A.P. Balasubramaniam, A. Peuronen, M. Lahtinen, M. Manickavachagam,
Crystallographic data have been deposited with the Cambridge
Crystallographic Data Centre as supplementary publication CCDC-
2046729, 2046730, 2046731 for 1, 2 and 3, respectively. Copies of
the data can be obtained free of charge on application to CCDC, 12
Union Road, Cambridge CB2 1EZ, UK [E- mail: deposit@ccdc.cam.ac.
uk]. Supplementary data to this article can be found online at htt
ps://doi.org/10.1016/j.ica.2021.120382.
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