New mono and dinuclear arene ruthenium chloro complexes containing ester substituents

Article abstract of DOI:10.1016/j.ica.2006.06.006

The dinuclear arene ruthenium complexes [RuCl₂{C₆H₅(CH₂)₃ OCO-p-C₆H₄-OC₈H₁₇}] ₂ (1) and [RuCl₂{p-C₆H₄(CH₂COOCH ₂CH₃)₂}]₂ (2) have been obtained by dehydrogenation of the corresponding cyclohexadiene derivative with ruthenium chloride hydrate. The single-crystal X-ray structure analysis of 2 shows the arene ligands to be involved in slipped-parallel π-π stacking interactions with neighbouring molecules, thus forming infinite chains along the b-axis. The dinuclear complexes 1 and 2 react with two equivalents of triphenylphosphine (PPh₃) to give in excellent yield the corresponding mononuclear phosphine complexes [RuCl₂{C₆H₅(CH₂)₃ OCO-p-C₆H₄-OC₈H₁₇} (PPh₃)] (3) and [RuCl₂{p-C₆H₄(CH₂ COOCH₂CH₃)₂}(PPh₃)] (4), respectively. The single-crystal X-ray structure analysis of 4 reveals the formation of a dimer through two C-H?Cl interactions in the solid state.

Full text of DOI:10.1016/j.ica.2006.06.006

Inorganica Chimica Acta 359 (2006) 4350–4354
www.elsevier.com/locate/ica
New mono and dinuclear arene ruthenium chloro complexes
containing ester substituents
*
Bruno Therrien , Georg Suss-Fink
¨
ˆ ˆ
Institut de Chimie, Universite´ de Neuchatel, Case postale 158, CH-2009 Neuchatel, Switzerland
Received 12 May 2006; accepted 2 June 2006
Available online 13 June 2006
Abstract
The dinuclear arene ruthenium complexes [RuCl2{C6H5(CH2)3OCO-p-C6H4-OC8H17}]2 (1) and [RuCl2{p-C6H4(CH2COOCH2-
CH3)2}]2 (2) have been obtained by dehydrogenation of the corresponding cyclohexadiene derivative with ruthenium chloride hydrate.
The single-crystal X-ray structure analysis of 2 shows the arene ligands to be involved in slipped-parallel p–p stacking interactions with
neighbouring molecules, thus forming infinite chains along the b-axis. The dinuclear complexes 1 and 2 react with two equivalents of
triphenylphosphine (PPh3) to give in excellent yield the corresponding mononuclear phosphine complexes [RuCl2{C6H5-
(CH2)3OCO-p-C6H4-OC8H17}(PPh3)] (3) and [RuCl2{p-C6H4(CH2COOCH2CH3)2}(PPh3)] (4), respectively. The single-crystal X-ray
structure analysis of 4 reveals the formation of a dimer through two C–Hꢀ ꢀ ꢀCl interactions in the solid state.
ꢀ 2006 Elsevier B.V. All rights reserved.
Keywords: Arene ligands; Chloro bridges; Dinuclear complexes; Phosphine ligands; Ruthenium
1. Introduction
Herein, we report the synthesis and molecular structure
of new functionalised dinuclear arene ruthenium complexes
containing ester substituents [RuCl2{C6H5(CH2)3OCO-p-
C6H4-OC8H17}]2 (1) and [RuCl2{p-C6H4(CH2COOCH2-
CH3)2}]2 (2), and their corresponding mononuclear
triphenylphosphine derivatives [RuCl2{C6H5(CH2)3OCO-
p-C6H4-OC8H17}(PPh3)] (3) and [RuCl2{p-C6H4(CH2COO
CH2CH3)2}(PPh3)] (4), respectively. The potential meso-
morphism properties of 1 and 3 are discussed, and the
single-crystal X-ray structure analyses of 2 and 4 are
presented.
The introduction of functionalised arene ligands in
arene ruthenium complexes has been motivated mainly
by the possibility of using the functionalised side-chain as
coordinating group: examples of chelating side-chains at
arene ligands include amines [1], alcohols [2], arsines [3],
carboxylic acids [4], thioethers [5], and phosphines [6].
However, few examples of functionalised arene ruthenium
complexes with non-chelating side-chains are known, they
have found applications in arene exchange [6a], electro-
chemistry [7], polymerisation [8], peptide labelling [4] or
resolution of racemates [9]. Therefore, we were interested
in the synthesis of mono- and di-functionalised arene
ruthenium complexes containing ester substituents as
potential entry to the synthesis of metal containing liquid
crystals.
2. Results and discussion
Two different strategies are used to form functionalised
dinuclear arene ruthenium complexes containing ester sub-
stituents. Both imply an esterification reaction, in which the
esterification is done either prior to the coordination of the
arene ligand (1), or simultaneously with the coordination of
the arene ligand (2), see Scheme 1. The dinuclear arene
ruthenium complex [RuCl2{C6H5(CH2)3OCO-p-C6H4-
OC8H17}]2 (1) is synthesised by standard dehydrogenation
*
Corresponding author.
E-mail address: bruno.therrien@unine.ch (B. Therrien).
0020-1693/$ - see front matter ꢀ 2006 Elsevier B.V. All rights reserved.
doi:10.1016/j.ica.2006.06.006

B. Therrien, G. Su¨ss-Fink / Inorganica Chimica Acta 359 (2006) 4350–4354
4351
OC8H17
O
O
OC8H17
RuCl3 . x H2O
Ru
Cl
O
O
1
Cl
Cl
Cl
O
EtOH, 80˚C
Ru
OC8H17
O
O
O
OH
C2H5O
OC2H5
O
RuCl3 . x H2O
Ru
Cl
2
Cl
Cl
Cl
EtOH, 80˚C
Ru
O
C2H5O
OC2H5
OH
O
O
Scheme 1.
of the appropriate cyclohexadiene with RuCl3 Æ x H2O in
refluxing alcohol [10]. 3-(Cyclohexa-1,4-dienyl)propyl-4-
(octyloxy)benzoate is prepared by standard esterification
method [11] from 3-(cyclohexa-1,4-dienyl)propan-1-ol [2b]
and 4-(octyloxy)benzoic acid.
By contrast, [RuCl2{p-C6H4(CH2COOCH2CH3)2}]2 (2)
is obtained by treatment of cyclohexa-1,4-diene-1,4-dicar-
boxylic acid with RuCl3 Æ x H2O in refluxing ethanol. The
carboxylic acid functions react with the solvent to form
the corresponding di-ester derivative. This particular
behaviour has been previously observed during the
reaction of cyclohexa-1,4-dienecarboxylic acid with
RuCl3 Æ x H2O in refluxing ethanol, affording the dinuclear
complex [RuCl2(C6H5CH2COOCH2CH3)]2 [4]. Com-
pounds 1 and 2 are air-stable orange solids, which have
Fig. 1. ORTEP drawing of [RuCl2{p-C6H4(CH2COOCH2CH3)2}]2 (2),
displacement ellipsoids are drawn at the 50% probability level and the
1
˚
been unambiguously characterised by H NMR, infrared
and mass spectrometry.
hydrogen atoms are omitted for clarity. Selected bond lengths (A) and
bond angles (ꢁ): Ru(1)–Ru(1)i 3.662(1), Ru(1)–Cl(1) 2.4070(11), Ru(1)–
Cl(2) 2.4427(12), Ru(1)–Cl(2)i 2.4305(9); Ru(1)–Cl(2)–Ru(1)i 97.43(4),
Cl(1)–Ru(1)–Cl(2) 86.59(4), C(1)–C(7)–C(8) 114.7(3), C(4)–C(11)–C(12)
113.0(3) (i = ꢁx, ꢁy, 1ꢁz).
The single-crystal X-ray structure analysis of 2 shows
the ruthenium atoms to be in a distorted octahedral geom-
etry, surrounded by the diethyl 2,20-(1,4-phenylene)diace-
tate ligand, a terminal chlorine atom and two bridging
chlorine atoms. Selected bond lengths and bond angles
are given in the caption of Fig. 1. The tethered arms point
away from the aromatic plane and the metrical parameters
around the metallic cores compare well with those of sim-
ilar dinuclear arene ruthenium [RuCl2(arene)]2 complexes
[6a,12]. The OCO bond angles of the two carboxylato pen-
dants [123.9(4)ꢁ and 124.3(4)ꢁ] differ only slightly from
those observed in other functionalised arene ruthenium
complexes with ester substituents [6a,6i,8b,13].
rings of the arene ligands. The p-stacking interacting sys-
tems form a series of one-dimensional supramolecular mul-
timers along the b-axis, see Fig. 2. The distance observed
between the p–p interacting systems (centroidꢀ ꢀ ꢀcentroid
˚
4.21 A) is slightly longer than the theoretical value calcu-
lated for this stacking mode [14].
The dinuclear ruthenium complexes 1 and 2 react with
two equivalents of PPh3 in dichloromethane to give in
excellent yield the mononuclear triphenylphosphine com-
plexes [RuCl2{C6H5(CH2)3OCO-p-C6H4-OC8H17}(PPh3)]
(3) and [RuCl2{p-C6H4(CH2COOCH2CH3)2}(PPh3)] (4),
respectively (Scheme 2). The composition and structure
The packing arrangement in the crystal is quite interest-
ing. Despite the presence of two side-arms, slipped-parallel
p-stacking interactions are observed involving the phenyl

4352
B. Therrien, G. Su¨ss-Fink / Inorganica Chimica Acta 359 (2006) 4350–4354
Fig. 2. Part of an infinite chain of 2 along the b-axis.
of the products have been determined by 1H, 31P{1H}
NMR, infrared and mass spectrometry.
Fig. 3. ORTEP drawing of [RuCl2{p-C6H4(CH2COOCH2CH3)2}(PPh3)]
(4), displacement ellipsoids are drawn at the 50% probability level and the
hydrogen atoms are omitted for clarity. Selected bond lengths (A) and
bond angles (ꢁ): Ru(1)–Cl(1) 2.4110(16), Ru(1)–Cl(2) 2.4037(19), Ru(1)–
P(1) 2.354(2); Cl(1)–Ru(1)–Cl(2) 89.33(6), P(1)–Ru(1)–Cl(1) 88.37(7),
P(1)–Ru(1)–Cl(2) 86.99(7), C(1)–C(7)–C(8) 113.0(6), C(4)–C(11)–C(12)
120.8(9).
The formation of complexes 3 and 4 is conveniently
monitored by 31P{1H} NMR spectroscopy. Each 31P{1H}
NMR spectrum shows singlets at 28.7 and 24.2 ppm,
respectively, the chemical shift being comparable to those
observed for the analogous triphenylphosphine arene
ruthenium complexes [RuCl2(C6H5Fc)(PPh3)] (Fc = ferro-
cene carboxylic acid phenethyl ester) [13] and [RuCl2
(C6Et6)(PPh3)] [15] which show signals at 28.6 and
24.0 ppm, respectively. Compound 4 is an orange air-stable
crystalline substance, the single-crystal X-ray analysis of
which shows the expected molecular structure, see Fig. 3.
Two neighbouring molecules form in the solid state a
weak hydrogen-bonded dimer, see Fig. 4. The Cl–C dis-
tances of the hydrogen bonds are, respectively, 3.393(9)
˚
˚
and 3.613(9) A, with C–Hꢀ ꢀ ꢀCl angles of 159.0ꢁ and
134.3ꢁ. The total distance between the two ruthenium
˚
atoms is 5.547(2) A.
The thermal behaviour of 1 and 3 has been studied in
view of possible mesomorphic properties. However, both
complexes decompose without apparition of liquid crystal-
line phases. The orange compound 1 decomposes at 205 ꢁC
to give a black solid. In the case of 3, the decomposition
occurs at lower temperature (155 ꢁC) and is accompanied
by the emergence of dark red bubbles in a liquid phase,
suggesting cleavage of the tethered ester chain and forma-
tion of a ruthenium compound which is then soaked in the
organic liquid phase.
Fig. 4. Hydrogen-bonded network between two symmetry related mole-
cules of 4.
3. Experimental
3.1. General
All organic solvents were degassed and saturated with
nitrogen prior to use. 4-(Octyloxy)benzoic acid was pur-
chased from Acros Organics and ruthenium chloride
hydrate was generously given by Johnson Matthey.
3-(Cyclohexa-1,4-dienyl)propan-1-ol [2b] and cyclohexa-
1,4-diene-1,4-dicarboxylic acid [16] were prepared accord-
ing to published methods. NMR spectra were recorded
on a Varian 200 MHz spectrometer. IR spectra were
recorded on a Perkin–Elmer 1720X FT-IR spectrometer
(4000–400 cmꢁ1). Microanalyses were performed by the
Laboratory of Pharmaceutical Chemistry, University of
Geneva (Switzerland). Electro-spray mass spectra were
obtained in positive-ion mode with an LCQ Finnigan mass
spectrometer.
CH2Cl2
[RuCl2(arene)]2 + 2 PPh3
2 RuCl2(arene)(PPh3)]
3-4
1-2
O
O
O
O
OC2H5
C2H5O
Ru
Ru
OC8H17
Cl
Cl
PPh3
PPh3
Cl
Cl
3
4
Scheme 2.

B. Therrien, G. Su¨ss-Fink / Inorganica Chimica Acta 359 (2006) 4350–4354
4353
Table 1
3.2. Syntheses
Crystallographic and selected experimental data of 2 and 4
Compound
2
4
3.2.1. Synthesis of 3-(cyclohexa-1,4-dienyl)propyl-4-
(octyloxy)benzoate
Chemical formula
Formula weight
Crystal system
C28H36Cl4O8Ru2
844.51
triclinic
C32H33Cl2O4PRu
684.52
triclinic
A solution of 4-(octyloxy)benzoic acid (1.8 g, 7.2 mmol),
N,N-dicyclohexylcarbodiimide (2.24 g, 10.9 mmol), 4-(di-
methylamino)pyridine (1.32 g, 10.8 mmol) and (cyclo-
hexa-1,4-dienyl)propan-1-ol (1.0 g, 7.2 mmol) in CH2Cl2
(80 mL) was stirred under nitrogen at room temperature
during 3 days. The resulting solution was filtered through
Celite to remove N,N-dicyclohexylurea, and the filtrate
was concentrated under reduced pressure. A chromato-
gram of the residue was recorded on a silica gel column,
eluting with hexane/CH2Cl2 (1:1). The pure product was
isolated from the first fraction, giving 3-(cyclohexa-1,4-die-
nyl)propyl-4-(octyloxy)benzoate as a white solid. Yield:
2.54 g (95%).
ꢀ
ꢀ
Space group
P1
P1
Crystal colour and shape
Crystal size (mm)
orange and rod
0.45 · 0.18 · 0.10
6.3280(12)
10.684(2)
13.170(3)
67.41(2)
77.33(3)
77.50(2)
793.4(3)
1
173(2)
1.768
1.336
4.18 < 2h < 52.08
2899
yellow and rod
0.60 · 0.40 · 0.12
10.4018(13)
12.1841(15)
13.2542(17)
83.032(15)
71.654(14)
70.984(14)
1507.1(3)
2
173(2)
1.508
0.786
4.34 < 2h < 52.20
5527
˚
a (A)
˚
b (A)
˚
c (A)
a (ꢁ)
b (ꢁ)
c (ꢁ)
3
˚
V (A )
Z
T (K)
Dcalc (g cmꢁ3
)
l (mmꢁ1
)
1H NMR (200 MHz, CDCl3): d = 8.00 (d, 2H), 6.93 (d,
2H), 5.74 (m, 2H), 5.51 (m, 1H), 4.32 (t, 2H), 4.03 (t, 2H),
2.68 (m, 4H), 2.15 (m, 2H), 1.83 (m, 4H), 1.42 (m, 10H),
0.92 (t, 3H); IR (KBr): m(OCO) 1716.5 s cmꢁ1; ESI-MS:
369.1 [M+H]+. Anal. Calc. for C24H34O3 (368.51): C,
76.77; H, 9.13. Found: C, 77.20; H, 8.95%.
Scan range (ꢁ)
Unique reflections
Reflections used
[I > 2r(I)]
Rint
Final R indices
[I > 2r(I)]
2329
2309
0.0563
0.0903
R1 = 0.0294,
wR2 = 0.0616
R1 = 0.0464,
wR2 = 0.0698
1.014
R1 = 0.0518,
wR2 = 0.1126
R1 = 0.1311,
wR2 = 0.1341
0.759
R indices (all data)
3.2.2. Synthesis of [RuCl2{C6H5(CH2)3OCO-p-C6H4-
OC8H17}]2 (1)
Goodness-of-fit
Maximum and
minimum Dq (e A
0.718 and ꢁ1.043
0.480 and ꢁ1.030
To a solution of ruthenium trichloride hydrate (1.2 g,
4.9 mmol) in ethanol (40 mL) was added 3-(cyclohexa-1,4-
dienyl)propyl-4-(octyloxy)benzoate (18.0 g, 49.0 mmol),
and the mixture was refluxed for 12 h. The orange precipi-
tate was filtered, washed with ether, and dried under vac-
uum to give 1. Yield: 2.44 g (93%).
ꢁ3
˚
)
ture was stirred for 5 h. The orange solution was filtered
through Celite to eliminate insoluble degradation materi-
als. The solution was evaporated and the solid dried under
vacuum to give 3. Yield: 132 mg (82%).
1H NMR (200 MHz, CDCl3): d = 7.93 (d, 2H), 6.92 (d,
2H), 5.65 (m, 3H), 5.43 (d, 2H), 4.34 (t, 2H), 4.03 (t, 2H),
2.78 (q, 2H), 2.12 (q, 2H), 1.34 (m, 12H), 0.92 (t, 3H); IR
(KBr): m(OCO) 1715.0 s cmꢁ1; ESI-MS: 1047.2 [MꢁCl]+.
Anal. Calc. for C48H64Cl4O6Ru2 (1081.0): C, 53.33; H,
5.97. Found: C, 53.48; H, 6.15%.
1H NMR (200 MHz, CDCl3): d = 7.97 (d, 2H), 7.80 (m,
6H), 7.39 (m, 9H), 6.93 (d, 2H), 5.31 (d, 2H), 5.21 (dd, 2H),
4.62 (t, 1H), 4.37 (t, 2H), 4.04 (t, 2H), 2.84 (t, 2H), 2.16 (q,
2H), 1.82 (q, 2H), 1.34 (m, 10H), 0.92 (t, 3H); 31P{1H}
NMR (80 MHz, CDCl3): d = 28.7; IR (KBr): m(OCO)
1699.3 s cmꢁ1; ESI-MS: 825.1 [M+Na]+. Anal. Calc. for
C42H47Cl2O3PRu (802.8): C, 62.84; H, 5.90. Found: C,
63.21; H, 6.14%.
3.2.3. Synthesis of [RuCl2{p-C6H4(CH2COO-
CH2CH3)2}]2 (2)
To a solution of ruthenium trichloride hydrate (1.0 g,
4.1 mmol) in ethanol (40 mL) was added cyclohexa-1,4-
diene-1,4-dicarboxylic acid (6.80 g, 40 mmol), and the
mixture was refluxed overnight. The orange precipitate
was filtered, washed with ether, and dried under vacuum
to give 2. Yield: 1.55 g (90%).
3.2.5. Synthesis of [RuCl2{p-C6H4(CH2COO-
CH2CH3)2}(PPh3)] (4)
To a solution of 2 (1.0 g, 1.2 mmol) in CH2Cl2 (20 mL)
was added PPh3 (650 mg, 2.5 mmol), and the mixture was
stirred for 6 h. The orange solution was filtered through
Celite to eliminate insoluble degradation materials. The
solution was evaporated and the solid dried under vacuum
to give 4. Yield: 1.1 g (67%).
1H NMR (200 MHz, CDCl3): d = 5.50 (s, 8H), 4.17 (q,
8H), 3.69 (s, 8H), 1.28 (t, 12H); IR (KBr): m(OCO) 1728.2
s
cmꢁ1
;
ESI-MS: 809.0 [MꢁCl]+. Anal. Calc. for
C28H36Cl4O8Ru2 (844.5): C, 39.82; H, 4.30. Found: C,
39.53; H, 4.45%.
1H NMR (200 MHz, CDCl3): d = 7.81 (m, 6H), 7.42 (m,
9H), 5.26 (s, 4H), 4.16 (q, 4H), 3.30 (s, 4H), 1.28 (t, 6H);
31P{1H} NMR (80 MHz, CDCl3): d = 24.2; IR (KBr):
m(OCO) 1726.5 s cmꢁ1; ESI-MS: 706.9 [M+Na]+, 649.0
[MꢁCl]+. Anal. Calc. for C32H33Cl2O4PRu (684.5): C,
56.15; H, 4.86. Found: C, 55.88; H, 4.73%.
3.2.4. Synthesis of [RuCl2{C6H5(CH2)3OCO-p-C6H4-
OC8H17}(PPh3)] (3)
To a solution of 1 (110 mg, 0.10 mmol) in CH2Cl2
(15 mL) was added PPh3 (55 mg, 0.21 mmol), and the mix-

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(f) A. Furstner, M. Liebl, C.W. Lehmann, M. Picquet, R. Kunz, C.
¨
3.3. X-ray crystallography
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Single-crystals of 2 and 4 were mounted on a Stoe Image
Plate Diffraction system equipped with a / circle goniom-
eter, using Mo Ka graphite monochromated radiation
˚
(k = 0.71073 A) with / range 0–200ꢁ, Dmax–Dmin
=
˚
12.45–0.81 A, increment of 1.8ꢁ and 1.2ꢁ, respectively.
The structures were solved by direct methods using the pro-
gram SHELXS-97 [17]. The refinement and all further calcu-
lations were carried out using SHELXL-97 [18]. In all
compounds the hydrogen atoms have been included in cal-
culated positions and treated as riding atoms using the
SHELXL default parameters. All non-H atoms were refined
anisotropically, using weighted full-matrix least-square on
F2. Crystallographic details are summarised in Table 1.
Figs. 1 and 3 are drawn with ORTEP [19] and Figs. 2
and 4 with MERCURY [20].
(q) K. Umezawa-Vizzini, T.R. Lee, Organometallics 22 (2003) 3066;
(r) P. Pinto, G. Marconi, F.W. Heinemann, U. Zenneck, Organo-
metallics 23 (2004) 374.
Acknowledgement
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Fink, J. Organomet. Chem. 689 (2004) 2456.
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The authors are grateful to the Fonds National Suisse de
la Recherche Scientifique for financial support.
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allics 22 (2003) 1894;
(c) L. Vieille-Petit, B. Therrien, A. Buryak, K. Severin, G. Su¨ss-Fink,
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Appendix A. Supplementary data
[9] L. VieilPetit, G. Suss-Fink, B. Therrien, T.R. Ward, H. Stoeckli-
¨
CCDC 607156 (2) and 607157 (4) contain the supple-
mentary crystallographic data for this paper. These data
can be obtained free of charge via www.ccdc.cam.ac.uk/
data_request/cif, by emailing data_request@ccdc.cam.
ac.uk, or by contacting The Cambridge Crystallographic
Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK
(fax: +44 1223 336 033). Supplementary data associated
with this article can be found, in the online version, at
doi:10.1016/j.ica.2006.06.006.
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