Synthesis and characterisation of the first cyanodiselenoimidocarbonate [C2N2Se2]2- complexes

Article abstract of DOI:10.1002/ejic.200400292

[Pt(C₂N₂Se₂)(PR₃)₂] (PR₃ = PMe₂Ph, PPh₃) and [Pt(C ₂N₂Se₂)(PP)] (PP = dppe, dppm, dppf) were obtained by the reaction of the appropria

Full text of DOI:10.1002/ejic.200400292

FULL PAPER
Synthesis and Characterisation of the First Cyanodiselenoimidocarbonate
[C2N2Se2]2؊ Complexes
Colin J. Burchell,[a] Stephen M. Aucott,[a] Alexandra M. Z. Slawin,[a] and
J. Derek Woollins*[a]
Keywords: Selenium / Platinum / Coordination modes
[Pt(C2N2Se2)(PR3)2]
(PR3
=
PMe2Ph,
PPh3)
and
anodiselenoimidocarbonate ligand is Se,Se-bidentate in the
monomeric complexes − the terminal CN group is approxim-
ately coplanar with the CSe2 group, and the nitrogen atom
is trigonal therefore reducing the planar symmetry of the li-
[Pt(C2N2Se2)(PP)] (PP = dppe, dppm, dppf) were obtained by
the reaction of the appropriate metal halide containing com-
plex with potassium cyanodiselenoimidocarbonate. The di-
meric cyanodiselenoimidocarbonate complexes [M{(C2- gands.
N2Se2)(η5-C5Me5)}2] (M = Rh Ir)] were synthesised from the
(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim,
appropriate transition metal dimer starting material. The cy-
Germany, 2005)
Introduction
complexes. Selected examples have been chosen for crystal-
lographic study.
The coordination of chalcogen donor ligands is an im-
portant area.[1Ϫ12] Sulfur-based ligands, especially S,S-bi-
Results and Discussion
dentate ligands, have
a
variety of industrial
applications.[9Ϫ12] Relative to the significant interest in sul-
fur donor ligands, the selenium analogues are a rather un-
derstudied area. Metal selenides and metal polyselenides
are well known and are readily prepared by direct reaction
of the elements. There has been significant interest in ZnSe
and CdSe semiconductors in photovoltaic devices because
of their intermediate energy bandgap.[13] Hence organomet-
allic compounds such as cadmium and zinc diselenocarba-
mato complexes[14] and selenoimidophosphonates[13] have
been investigated as single-source precursors for deposition
of these semiconductor materials. Other well-established
selenium donor ligands include the selenoethers[15Ϫ18] and
the pseudohalide selenocyanate.[19,20] However, there are
very few Se,Se-bidentate ligands reported in the literature,
which include a series of (diselenothiocarbonato)bis(phos-
phane)platinum compounds,[21] two triselenocarbonate
complexes [(η-5C5H5)Co(CSe3)(PMe3)][22] and [Ba(CSe3)],[23]
a (2,4-dioxo-3,3-pentanediselenolato)bis(phosphane)platinum
complex,[24] two diselenocarbonimidato compounds,[25,26]
[{CH[Si(CH3)3]2}2Sn(SeSe)PC6H2[C(CH3)3]3][27] and a series
of [Pt{Se2P(Se)(C6H5)}(PR3)2] complexes.[28] As part of our
program studying the properties of chalcogen donor sys-
tems we have recently reported a series of cyanodithio-
imidocarbonate complexes.[29] Here we describe the syn-
thesis of the corresponding cyanodiselenoimidocarbonate
The synthesis of dipotassium cyanodiselenoimidocarbon-
ate was reported by Jensen and Henriksen in 1970.[30] The
original synthesis involved the dropwise addition of potass-
ium hydroxide in water to cyanamide and carbon diselenide
in dioxane at 0 °C. Our synthesis is essentially the same
[Equation (1)], except the reaction was carried out in etha-
nol and potassium ethoxide was used in place of potassium
hydroxide to prevent the generation of water during the re-
action.
(1)
After suction filtration under nitrogen, the product was
obtained as an impure off-yellow solid. In the IR spectrum,
a strong ν(CϵN) band at 2127 cmϪ1 and a strong band at
1347 cmϪ1 assigned as ν(CϭN) are observed. Purification
proved unsuccessful, hence the dipotassium cyanodiseleno-
imidocarbonate was used as obtained for subsequent reac-
tion.
The bis(phosphane)platinum complexes [Pt(C2N2Se2)-
(PR3)2] (PR3 ϭ PMe2Ph, PPh3) and [Pt(C2N2Se2)(PP)]
(PP ϭ dppe, dppm, dppf) were obtained by reaction of the
appropriate [PtCl2(PR3)2] or [PtCl2(PP)] complex with ex-
cess potassium cyanodiselenoimidocarbonate in tetrahydro-
furan. A large excess of the dipotassium salt was used as
[a]
School of Chemistry, University of St. Andrews,
St. Andrews, Fife KY16 9ST, UK
E-mail: jdw3@st-andrews.ac.uk
Eur. J. Inorg. Chem. 2005, 209Ϫ213
DOI: 10.1002/ejic.200400292
© 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
209

C. J. Burchell, S. M. Aucott, A. M. Z. Slawin, J. D. Woollins
FULL PAPER
this gave a cleaner reaction. The solvent was evaporated parable examples are [PtSe2C2(CO2CH3)2(PPh3)2][31]
under reduced pressure, and dichloromethane was added. [2J(31PϪ77Se)
52 Hz],
[Pt{C6H2(CF3)3}Se]2(PPh3)2][32]
The mixture was filtered through a Celite pad to remove [2J(31PϪ77Se) 47 Hz] and [(CO)6Fe2(µ3-Se)2Pt(PPh3)2][33]
precipitated KCl and any residual dipotassium cyanodise- [2J(31PϪ77Se) 24 Hz]. The X-ray crystal structures of both
lenoimidocarbonate, and the filtrate was then concentrated 1 (Table 3, Figure 1) and 3 (Table , Figure 2) were obtained.
to dryness to give the product [Equation (2)].
In both examples, the X-ray analysis shows that the plati-
num core lies at the centre of a distorted square-planar co-
ordination sphere. The distortion from idealised square-
planar geometry (90°) can be illustrated by the
P(1)ϪPt(1)ϪP(2) bond angle of 94.46(9)° in 1 and 86.64(8)°
in 3. The corresponding Se(1)ϪPt(1)ϪSe(2) bite angles in 1
and 3 are 77.37(4)° and 77.81(3)°, respectively. In the
PtSe2C ring for 1, the PtϪSeϪC angles are 86.1(3)° and
86.9(3)°. The Se(1)ϪC(1)ϪSe(2) angle is 109.5(5)°. In com-
pound 3, the PtϪSeϪC angles are 86.1(2)° and 85.9(2)°.
The Se(1)ϪC(1)ϪSe(2) angle is 110.2(4)°. The nonbonded
selenium distance is 3.08 A and 3.09 A for 1 and 3, respec-
tively, and both these values correspond to about 81% of
the van der Waals radii of selenium, which implies that
there is a significant interaction between the two selenium
atoms. As observed in the sulfur analogues, N(1) is trigonal
therefore reducing the planar symmetry of the ligand in
both 1 and 3. In 1, the cyanodiselenoimidocarbonate ligand
lies within the coordination plane with the exception of
C(1)ϪN(1)ϪC(2)ϪN(2), which is hinged at an angle of 9°
to the plane. In 3, the whole complex is almost planar, how-
ever, there is a small hinge angle of 2° with respect to the
(2)
˚
˚
The microanalyses of all compounds were satisfactory,
and all compounds showed the anticipated [Mϩ] peak in
their mass spectra (Table 1). The ν(CϵN) vibrations are ob-
served in the range 2174Ϫ2179 cmϪ1, and the ν(CϭN) vi-
brations can be seen in the region of 1492Ϫ1495 cmϪ1
(Table 2); these values are comparable with the correspond-
ing (cyanodithioimidocarbonate)bis(phosphane)platinum
complexes.[29] The ν(PtϪSe) bands all lie within the range
246Ϫ294 cmϪ1 (Table 2). The (cyanodiselenoimidocarbona-
te)bis(phosphane)platinum complexes 1Ϫ5 (Table 2) all
show sharp singlets with platinum and selenium satellites in
coordination plane.
The dimeric cyanodiselenoimidocarbonate complexes
their 31P{1H} NMR spectra, and have similar δ values to [M{(C2N2Se2)(η5-C5Me5)}2] [M ϭ Rh (6), Ir (7)] were syn-
the sulfur analogues.[29] The 1J(195PtϪ31P) coupling con- thesised and isolated in a similar manner to the (cyanodise-
stants lie in the range 2620Ϫ3263 Hz, and the variations lenoimidocarbonate)bis(phosphane)platinum
complexes
reflect the nature of the phosphane group. In all the com- 1Ϫ5 by reaction of excess dipotassium salt with the appro-
plexes, cis and trans 2J(31PϪ77Se) couplings can be observed priate transition metal dimer starting material [Equa-
(Table 2). The values noted are of similar magnitude to tion (3)].Compounds 6 and 7 both gave satisfactory micro-
those found in the literature for bis(phosphane)platinum analyses and show the anticipated [Mϩ] peak in their mass
complexes containing selenium donor ligands. Some com- spectra (Table 1). The ν(CϵN) vibrations are observed at
Table 1. Microanalytical (calculated values in parentheses) and mass spectrometric data for complexes 1Ϫ7
Complex
C
H
N
m/z
682
931
804
791
960
898
1077
1 [Pt(C2N2Se2)(PMe2Ph)2]
2 [Pt(C2N2Se2)(PPh3)2]
3 [Pt(C2N2Se2)(dppe)]
4 [Pt(C2N2Se2)(dppm)]·CH2Cl2
5 [Pt(C2N2Se2)(dppf)]·CH2Cl2
6 [{Rh(C2N2Se2)(η5-C5Me5)}2]
7 [{Ir(C2N2Se2)(η5-C5Me5)}2]
31.60 (31.73)
49.41 (49.10)
41.88 (41.86)
38.89 (38.46)
42.83 (42.55)
32.44 (32.17)
27.21 (26.82)
3.01 (3.25)
2.85 (3.25)
2.79 (3.01)
2.68 (2.77)
2.64 (2.69)
3.77 (3.37)
2.39 (2.81)
3.83 (4.11)
2.76 (3.01)
3.29 (3.49)
3.13 (3.20)
2.37(2.68)
5.76 (6.25)
5.65 (5.21)
Table 2. 31P{1H} NMR (109.4 MHz) and selected IR data for complexes 1Ϫ5
Complex
δ(P) [ppm] 1J(195PtϪ31P) [Hz] 2J(77SeϪ31P) [Hz] ν(CϵN) [cmϪ1
]
ν(CϭN) [cmϪ1
]
ν(Pt-Se) [cmϪ1
]
1 [Pt(C2N2Se2)(PMe2Ph)2] Ϫ19.6
3063
3190
3049
2620
3263
42, 23
68, 42
73, 49
40, 19
47, 28
2179
2177
2178
2175
2174
1494
1497
1492
1492
1495
294, 254
282, 246
280, 246
282, 258
279, 252
2 [Pt(C2N2Se2)(PPh3)2]
3 [Pt(C2N2Se2)(dppe)]
4 [Pt(C2N2Se2)(dppm)]
5 [Pt(C2N2Se2)(dppf)]
17.3
44.8
Ϫ54.2
16.4
210
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Eur. J. Inorg. Chem. 2005, 209Ϫ213

Synthesis and Characterisation of the First Cyanodiselenoimidocarbonate [C2N2Se2]2Ϫ Complexes
FULL PAPER
˚
Table 3. Selected bond lengths [A] and angles [°] for compounds 1
and 3
Compound
1
3
Pt(1)ϪP(1)
Pt(1)ϪP(2)
Pt(1)ϪSe(1)
Pt(1)ϪSe(2)
Se(1)ϪC(1)
Se2)ϪC(1)
C(1)ϪN(1)
N(1)ϪC(2)
2.271(2)
2.266(3)
2.4570(12)
2.4725(11)
1.916(9)
1.856(10)
1.305(13)
1.329(13)
1.184(12)
77.37(4)
2.245(2)
2.236(2)
2.4577(9)
2.4617(9)
1.880(8)
1.886(7)
1.333(9)
1.350(10)
1.167(10)
77.81(3)
86.64(8)
C(2)ϪN(2)
Se(1)ϪPt(1)ϪSe(2)
P(1)ϪPt(1)ϪP(2)
Se(1)ϪC(1)ϪN(1)
Se(2)ϪC(1)ϪN(1)
Pt(1)ϪSe(1)ϪC(1)
Pt(1)ϪSe(2)ϪC(1)
P(1)ϪPt(1)ϪSe(1)
P(2)ϪPt(1)ϪSe(2)
C(1)ϪN(1)ϪC(2)
N(1)ϪC(2)ϪN(2)
94.46(9)
126.6(7)
123.9(7)
86.1(3)
127.9(6)
121.8(6)
86.1(2)
86.9(3)
85.9(2)
Figure 2. Crystal structure of 3
92.96(7)
95.11(7)
119.1(8)
175.9(12)
95.71(6)
99.83(6)
115.0(6)
175.8(9)
Experimental Section
General: Unless otherwise stated, operations were carried out under
oxygen-free nitrogen by using standard Schlenk techniques. All
solvents and reagents were purchased from Aldrich, Alfa Aesar,
BDH, Fisons and Strem and used as received. We are grateful to
Johnson Matthey PLC for the loan of the precious metal salts.
Diethyl ether and tetrahydrofuran were purified by reflux in the
presence of sodium/benzophenone and by distillation under nitro-
gen. Hexane was purified by reflux in the presence of sodium and
by distillation under nitrogen. Dichloromethane was heated to re-
flux in the presence of powdered calcium hydride and distilled un-
der nitrogen. CD2Cl2 (99.6ϩ atom D) was used as received. Carbon
diselenide was prepared as a dichloromethane solution by passing
dichloromethane over elemental selenium at 600 °C.[34,35] The metal
complexes [{RhCl(µ-Cl)(η5-C5Me5)}2][36] and [{IrCl(µ-Cl)(η5-
C5Me5)}2][36] were prepared according to literature procedures. The
complexes [PtCl2(PMe2Ph)2], [PtCl2(PPh3)2], [PtCl2(dppe)] [dppe ϭ
bis(diphenylphosphanyl)ethane], [PtCl2(dppm)] and [PtCl2(dppf)]
[dppf ϭ bis(diphenylphosphanyl)ferrocene] were prepared by the
addition of stoichiometric quantities of the appropriate free phos-
phane or diphosphane to
a dichloromethane solution of
[PtCl2(cod)] (cod ϭ cycloocta-1,5-diene). Infrared spectra were re-
corded (IR spectra as KBr discs, unless otherwise stated) with a
PerkinϪElmer System 2000 FT/IR/Raman spectrometer. 31P, 13C
and 1H NMR spectra were recorded with a JEOL DELTA GSX
270 FT NMR spectrometer. Microanalysis was performed by the
University of St. Andrews service. Fast atom bombardment (FAB)
and electron ionisation (EI) mass spectra were performed by the
EPSRC National Mass Spectrometer service.
Figure 1. Crystal structure of 1
approximately 2180 cmϪ1, and the ν(CϭN) vibrations can
be seen in the region of 1459Ϫ1492 cmϪ1. The bands for
ν(MϪSe) are all observed in the range 240Ϫ282 cmϪ1
.
[Pt(C2N2Se2)(PMe2Ph)2] (1): [PtCl2(PMe2Ph)2] (0.050 g, 0.0769
mmol) was dissolved in THF (20 mL), and potassium cyanodise-
lenoimidocarbonate (0.167 g, 0.580 mmol) was added as a solid in
one portion. The resulting orange solution was stirred in the ab-
sence of light for 48 h. The solvent was evaporated in vacuo, and
the remaining solid was extracted with dichloromethane (20 mL).
The mixture was filtered through a Celite pad to remove precipi-
tated KCl and washed with additional dichloromethane (30 mL).
The filtrate was concentrated to dryness in vacuo to give a pale
orange powder. The following compounds 2Ϫ7 were prepared and
worked up in the same manner as platinum complex 1. The product
was recrystallised by vapour diffusion from chloroform/hexane to
give X-ray quality crystals. Yield 0.027 g (52%). 1H NMR
(3)
Eur. J. Inorg. Chem. 2005, 209Ϫ213
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211

C. J. Burchell, S. M. Aucott, A. M. Z. Slawin, J. D. Woollins
Table 4. Details of the X-ray data collections and refinements for compounds 1 and 3
FULL PAPER
Compound
1
3
Empirical formula
Crystal dimensions [mm]
Crystal system
C18H22N2P2PtSe2
0.1 ϫ 0.03 ϫ 0.03
monoclinic
C2/c
33.596(8)
11.542(3)
10.974(3)
91.536(5)
4253.5(19)
8
C28H24N2P2PtSe2
0.13 ϫ 0.05 ϫ 0.05
monoclinic
P21/n
12.1941(18)
18.081(3)
12.6978(19)
105.898(3)
2692.6(7)
4
Space group
˚
a [A]
˚
b [A]
˚
c [A]
β [°]
3
˚
V [A ]
Z
M
681.33
2.128
10.175
803.44
1.982
8.054
Dc [g·cmϪ3
]
µ [mmϪ1
]
Measured reflections
Independent reflections (Rint
Final R1, wR2 [I Ͼ 2σ(I)]
13027
3804 (0.0937)
0.0426, 0.0687
11392
3816 (0.0613)
0.0314, 0.0533
)
(CD2Cl2): δ ϭ 1.63 [d, 3J(195PtϪ1H) ϭ 36 Hz, 2J(31PϪ1H) ϭ 10 Hz, the heavy atom method or by direct methods. The positions
12 H, PMe], 7.48Ϫ7.69 (m, 10 H, aromatic H) ppm.
of the hydrogen atoms were idealised. Refinements were by
full-matrix least squares based on F2 using SHELXTL.[37] CCDC-
233740 and -233741 contain the supplementary crystallographic
data for this paper. These data can be obtained free of charge at
www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge
CB2 1EZ, UK; Fax: (internat.) ϩ 44-1223-336-033; E-mail:
deposit@ccdc.cam.ac.uk].
[Pt(C2N2Se2)(PPh3)2] (2): [PtCl2(PPh3)2] (0.050 g, 0.0632 mmol)
and potassium cyanodiselenoimidocarbonate (0.208 g, 0.722
mmol) gave the product as a beige powder. Yield 0.029 g (49%). 1H
NMR (CD2Cl2): δ ϭ 7.24Ϫ7.52 (m, 30 H, aromatic H).
[Pt(C2N2Se2)(dppe)] (3): [PtCl2(dppe)] (0.060 g, 0.0903 mmol) and
potassium cyanodiselenoimidocarbonate (0.227 g, 0.788 mmol)
gave the product as an orange powder. The product was recrystal-
lised by vapour diffusion from chloroform/hexane to give X-ray
quality crystals. Yield 0.049 g (67%). 1H NMR (CD2Cl2): δ ϭ
2.40Ϫ2.59 (m, 4 H, PCH2CH2P), 7.48Ϫ7.69 (m, 20 H, aromatic
H) ppm.
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[Pt(C2N2Se2)(dppm)] (4): [PtCl2(dppm)] (0.060 g, 0.0923 mmol) and
potassium cyanodiselenoimidocarbonate (0.211 g, 0.732 mmol)
gave the product as a yellow powder. Yield 0.022 g (30%). 1H NMR
(CD2Cl2): δ ϭ 3.89Ϫ4.18 (m, 2 H, PCH2P), 7.25Ϫ7.71 (m, 20 H,
aromatic H) ppm.
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[Pt(C2N2Se2)(dppf)] (5): [PtCl2(dppf)] (0.080 g, 0.0975 mmol) and
potassium cyanodiselenoimidocarbonate (0.085 g, 0.295 mmol)
gave the product as a yellow powder. Yield 0.044 g (45%). 1H NMR
(CD2Cl2): δ ϭ 4.36 [br. m, 4 H, β-CH (C5H4)], 4.44 [br. m, 4 H, α-
CH (C5H4)], 7.36Ϫ7.88 (m, 20 H, aromatic) ppm.
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[{RhCl(µ-Cl)(η5-C5Me5)}2]
[11]
(0.060 g, 0.0971 mmol) and potassium cyanodiselenoimidocarbon-
ate (0.359 g, 1.246 mmol) gave a very dark red powder. Yield
0.037 g (42%). 1H NMR (CD2Cl2): δ ϭ 1.54Ϫ1.89(m, 30 H, η5-
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0.0502 mmol) and potassium cyanodiselenoimidocarbonate
(0.268 g, 0.9308 mmol) gave an orange powder. Yield 0.021 g
(39%). 1H NMR (CD2Cl2): δ ϭ 1.57Ϫ1.86 (m, 30 H, η5-C5Me5)
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Synthesis and Characterisation of the First Cyanodiselenoimidocarbonate [C2N2Se2]2Ϫ Complexes
FULL PAPER
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