Synthesis and molecular structure of the novel bismuth(III) sulfonate complex [Bi(C18H14P(O)SO3)2 (DMSO) 3](NO3)·DMSO·2H2O

Article abstract of DOI:10.1515/mgmc-2012-0049

The synthesis of [Bi(C₁₈H₁₄P(O)SO₃) ₂(DMSO)₃] (NO₃)·DMSO·2H ₂O starting from [Bi₆O₄(OH)₄] (NO₃)₆·H₂O and 2-(diphenylphosphino) benzenesulfonic acid is presented.³¹P{¹H }-NMR experiments confirm the in situ oxidation of 2-(diphenylphosphino)benzenesulfonic acid to give 2-(diphenylphosphine oxide)benzenesulfonic acid by heating in dimethyl sulfoxide (DMSO). In the presence of [Bi₆O₄(OH) ₄](NO₃)₆·H₂O, subsequent formation of single crystals of the title compound is observed. The crystal structure determination reveals that the bismuth atom shows a [5 + 4] coordination with short Bi-O distances in the range of 2.278(11) to 2.398(11) A to the oxygen atoms of DMSO and phosphine oxide groups and with longer Bi-O bonds of 2.74(2) and 2.88(2) A to the chelating sulfonate groups.

Full text of DOI:10.1515/mgmc-2012-0049

DOI 10.1515/mgmc-2012-0049ꢀ
ꢀMain Group Met. Chem. 2012; 35(5-6): 135–139
Maik Schlesinger, Tobias Rüffer, Heinrich Lang and Michael Mehring*
Synthesis and molecular structure of the novel
bismuth(III) sulfonate complex
[Bi(C18H14P(O)SO3)2(DMSO)3](NO3)‧DMSO‧2H2O
Abstract: The synthesis of [Bi(C18H14P(O)SO3)2(DMSO)3] DE-NOL™ (Sun, 2011). Furthermore, bismuth subnitrate
(NO3)‧DMSO‧2H2O starting from [Bi6O4(OH)4](NO3)6‧H2O and bismuth subsalicylate as additional components in
and 2-(diphenylphosphino)benzenesulfonic acid is pre- triple and quadruple therapies based on antibiotics and
sented. 31P{1H}-NMR experiments confirm the in situ oxi- proton pump inhibitors (Dittes et al., 1997; Turel et al.,
dation of 2-(diphenylphosphino)benzenesulfonic acid to 1998; Phillips et al., 2000; Whitehead et al., 2000; Butcher,
give 2-(diphenylphosphine oxide)benzenesulfonic acid by 2003) are very active in the eradication of Helicobacter
heating in dimethyl sulfoxide (DMSO). In the presence of pylori, one of the main causes of gastritis and nausea.
[Bi6O4(OH)4](NO3)6‧H2O, subsequent formation of single Andrews et al. (2009) recently demonstrated that water-
crystals of the title compound is observed. The crystal struc- soluble bismuth complexes based on 5-sulfosalicylic acid
ture determination reveals that the bismuth atom shows a exhibit greater activity against H. pylori than commercial
[5+4] coordination with short BiϪO distances in the range bismuth subsalicylate. This demonstrates that soluble
of 2.278(11) to 2.398(11) Å to the oxygen atoms of DMSO and bismuth sulfonates might be key intermediates in obtain-
phosphine oxide groups and with longer BiϪO bonds of ing higher activity against bacteria. In addition to the
2.74(2) and 2.88(2) Å to the chelating sulfonate groups.
5-sulfosalicylate derivatives and the well-known bismuth
trifluoromethanesulfonate (Gaspard-Iloughmane and
Keywords: bismuth; bismuth oxido cluster; phosphine Le Roux, 2004), only a few other bismuth(III) sulfonates
oxide; sulfonate.
such as [Bi6O4(OH)4(OTf)6(CH3CN)6]‧2CH3CN (TfO- – triflate)
[Bi6O4(OH)4(O3SNH2)6], [Bi18O12(OH)12(O3S–Cam)18(H2O)2]
(Cam-SO — S-(+)-10-camphor sulfonate) and [Bi O (O S-
-
38
3
Mes) (H3O) ] (Mes-SO — mesitylene sulfonate)45 have
* Corresponding author: Michael Mehring, Technische Universität
Chemnitz, Institut für Chemie, Professur Koordinationschemie,
Straße der Nationen 62, D-09111 Chemnitz, Deutschland,
e-mail: michael.mehring@chemie.tu-chemnitz.de
Maik Schlesinger: Technische Universität Chemnitz, Institut für
Chemie, Professur Koordinationschemie, Straße der Nationen 62,
D-09111 Chemnitz, Deutschland
Tobias Rüffer and Heinrich Lang: Technische Universität Chemnitz,
Institut für Chemie, Professur Anorganische Chemie, Straße der
Nationen 62, D-09111 Chemnitz, Deutschland
-
3
been24 reported and structurally characterized so far
(Arnauld et al., 1997; Sharutin et al., 2002a,b; Andrews
et al., 2010, 2012; Miersch et al., 2011b). We report here
on the synthesis, crystal and molecular structure of
the novel bismuth(III) sulfonate complex [Bi(C18H14P(O)
SO3)2(DMSO)3](NO3)·DMSO‧2H2O, that was obtained upon
our attempts to synthesize polynuclear bismuth oxido
sulfonates.
2
14
Introduction
Bismuth-containing compounds have been used as
Results and discussion
medical agents since more than three centuries now The synthesis of the title compound starts from a dime-
(Briand and Burford, 1999; Mehring, 2007; Yang and Sun, thyl sulfoxide (DMSO) solution of [Bi6O4(OH)4](NO3)6‧H2O
2007). Especially the non-toxic nature of most compounds (Lazarini, 1979) and 2-(diphenylphosphino)benzenesul-
is one of the major driving forces for the increasing interest fonic acid at a temperature of 80°C. The 2-(diphenylphos-
in bismuth-containing materials and is mainly a result of phino)benzenesulfonic acid was in situ oxidized to the cor-
the often-observed low solubility of bismuth compounds responding phosphine oxide. In order to clarify the role of
in aqueous solution. Noteworthy, the so-called bismuth the bismuth oxido cluster in the oxidation process, nuclear
subsalicylate and bismuth subcitrate are used as compo- magnetic resonance (NMR)-based experiments without
nents in medical formulations such as Pepto-Bismol® and adding a bismuth source were carried out. The 31P{1H}-NMR
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ꢁꢁꢁꢂ
136ꢀ ꢀM. Schlesinger et al.: Synthesis and structure of a bismuth sulfonate
signal of a freshly prepared 2-(diphenylphosphino)benze- (Miersch et al., 2010). If DMSO is used as a solvent, we
nesulfonic acid solution in CDCl3 is observed at 3.4 ppm. did observe a growth of the hexanuclear bismuth oxido
However, in DMSO-d6, two 31P{1H}-NMR signals at -11.1 and cluster to give Bi38-oxido clusters such as [Bi38O45(NO3)20
34.2 ppm are observed approximately 1 h after dissolution. (DMSO)28](NO3)4‧4DMSO,[{Bi38O45(NO3)24(DMSO)26}‧4DMSO]
The latter signal is unambiguously assigned to 2-(diphe- [{Bi38O45-(NO3)24(DMSO)24}‧4DMSO],
[Bi38O45(OH)2(pTsO)8
nylphosphine oxide)benzenesulfonic acid and indicates (NO3)12(DMSO)24](NO3)2‧4DMSO ‧2H2O and [Bi38O45(OMc)24
the oxidation of phosphine to the appropriate phosphine (DMSO)9]‧2DMSO‧7H2O by adding nitric acid, sodium
oxide after dissolving the starting compound in DMSO-d6 toluene-4-sulfonate (pTsONa) and sodium methacrylate
at ambient temperature. After heating the NMR tube to (NaOMc) as additives, respectively (Miersch et al., 2011a,b,
80°C for 4 h, the 31P{1H}-NMR signal at 34.2 ppm is exclu- 2012). By contrast, under the reaction conditions used
sively observed. An in situ NMR experiment in DMSO-d6 here, the chelate effect of the 2-(diphenylphosphine oxide)
starting from Bi(NO3)3‧5H2O and 2-(diphenylphosphino) the benzenesulfonic acid favors the degradation of the hexa-
benzenesulfonic acid shows that bismuth salt decelerates nuclear bismuth oxido cluster [Bi6O4(OH)4](NO3)6 to give
the oxidation of the phosphine group. After 48 h at 80°C, the mononuclear title compound (Figure 1).
approximately 70% of the phosphine is oxidized to the
[Bi(C18H14P(O)SO3)2(DMSO)3](NO3)‧DMSO‧2H2O crys-
phosphine oxide and the title compound is formed. This tallizes in the monoclinic space group P21/m with two
is confirmed by a broad 31P{1H}-NMR chemical shift at 39.4 formula units per unit cell. The cell dimensions are
ppm (an additional signal at -11.1 ppm is observed for the a=9.5436(1) Å, b=18.2414(2) Å, c=15.1817(1) Å, β=90.434(1)°
non-coordinated 2-(diphenylphosphino)benzenesulfonic and V=2642.89(4) ų. The structure shows some disorder
acid), identical to that observed after the dissolution of of the 2-(diphenylphosphine oxide)benzenesulfonates
[Bi(C18H14P(O)SO3)2(DMSO)3](NO3)‧DMSO‧2H2O in DMSO-d6. and the non-coordinating DMSO that was refined prop-
A broad 31P{1H}-NMR signal at approximately 40 ppm is erly. The coordination sphere of bismuth shows a [5+4]
typical for metal-coordinated phosphine oxides (Mecking coordination which results in a square-based pseudo
and Keim, 1996; Levason et al., 2000; Saravanabharathi pyramid (Figure 2). The bismuth atom shows five primary
et al., 2002; Glazier et al., 2004; Farrer et al., 2010).
BiϪO bonds composed of three monodentate DMSO
The same reaction conditions were used in order to molecules with short BiϪO bond lengths in the range of
modify the periphery of the hexanuclear [Bi6O4(OH)4] 2.278(11) to 2.398(11) Å (Table 1) and of two coordinating
(NO3)6‧H2O cluster (Scheme 1). However, we did observe oxygen atoms of the phosphine oxides (BiϪO: 2.338(9) Å).
degradation of the cluster to give the mononuclear The BiϪO bond length of the coordinating phosphine
title compound as observed with a yield of 71% after oxide is in the same range as described for the bismuth
crystallization.
phosphine oxide complex [BiI2{OP(NMe2)3} 4][I5] reported
Our previous investigations towards the functionali- by Farrugia et al. (1998) (BiϪO: 2.317 Å). The pseudo
zation of [Bi6O4(OH)4](NO3)6‧H2O showed that, in toluene pyramid is capped by two asymmetrically coordinating
solution, an exchange of the nitrate ligands for trifluo- and chelating sulfonate groups (BiϪO: 2.74(2)–2.88(2)
romethanesulfonate to give [Bi6O4(OH)4(OTf)6] does occur Å). The BiϪO bond lengths of the sulfonate groups are
NO3
SO3H
A
PPh2
1. [DMSO], [O]
Ph2P
80°C, 4 h
+ 1/6 [Bi6O4(OH)4](NO3)6 H2O
O
S
O
S
2. Crystallization
2 months
(yield 71 %)
O
O
O
O
S
O
Bi
O
O
SO3H
SO3H
O
B
S
O
S
O
PPh2
PPh2
[DMSO],
80°C, 4 h
1. 1/6 [Bi6O4(OH)4](NO3)6 H2O
PPh2
[O]
2. Crystallization
2 months
Scheme 1ꢀSynthesis of [Bi(C18H14P(O)SO3)2(DMSO)3](NO3)‧DMSO‧2H2O by (A) a single step and (B) a sequential approach.
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M. Schlesinger et al.: Synthesis and structure of a bismuth sulfonateꢀ
ꢀ137
O(1)–Bi(1)
2.338(9)
2.815(19)
2.74(2)
2.81(3)
80.6(4)
73.6(3)
77.4(2)
72.0(4)
152.6(4)
94.5(3)
136.8(4)
82.9(4)
63.9(5)
129.2(5)
122.5(8)
O(3′)–Bi(1)a
2.88(2)
2.398(11)
2.296(11)
2.278(11)
69.7(7)
O(2)–Bi(1)
O(5)–Bi(1)
O(2′)–Bi(1)a
O(3)–Bi(1)
O(6)–Bi(1)
O(7)–Bi(1)
O(7)–Bi(1)–O(6)
O(7)–Bi(1)–O(1)
O(6)–Bi(1)–O(1)
O(7)–Bi(1)–O(5)
O(6)–Bi(1)–O(5)
O(1)–Bi(1)–O(5)
O(7)–Bi(1)–O(2′)
O(6)–Bi(1)–O(2′)
O(1)–Bi(1)–O(2′)
O(7)–Bi(1)–O(3)
O(6)–Bi(1)–O(3)
O(1)–Bi(1)–O(3)
O(5)–Bi(1)–O(3)
O(7)–Bi(1)–O(2)
O(6)–Bi(1)–O(2)
O(1)–Bi(1)–O(2)
O(3)–Bi(1)–O(2)
O(7)–Bi(1)–O(3′)
O(6)–Bi(1)–O(3′)
O(1)–Bi(1)–O(3′)
O(5)–Bi(1)–O(3′)
O(2′)–Bi(1)–O(3′)
77.2(7)
141.0(4)
75.7(4)
71.3(5)
49.8(7)
118.5(5)
126.6(5)
64.0(5)
69.4(5)
48.1(5)
Table 1ꢀSelected interatomic distances (Å) and angles (degrees) in
[Bi(C18H14P(O)SO3)2(DMSO)3](NO3)‧DMSO‧2H2O .
Figure 1ꢀMolecular structure of [Bi(C18H14P(O)SO3)2(DMSO)3]
(NO3)‧DMSO‧2H2O. Symmetry transformations used: A=x, 0.5-y, z.
Atomic positions of O2, O3, S1 and P1 are disordered (occupation
factor of 0.5). C and H atoms are omitted for clarity.
aAtomic positions of O2 and O3 are slightly disordered and have an
occupation factor of 0.5.
markedly longer than those reported for the bismuth sul- involved in strong hydrogen bonding. Absorption bands
fonate complexes [Ph2Bi(O3S–Mes)]∞, [Ph2Bi(O3S–Cam)]∞, at 1347 and 1068 cm-1 are assigned to νas(NO2) and νs(NO2)
[PhBi(O3S–Tol)2]∞ and [PhBi(O3S–Mes)2]∞, which all show of the nitrate ion.
monodentate coordination with BiϪO bond lengths of
A view along the crystallographic [100]-axis shows
approximately 2.4 Å (Andrews et al., 2010). Furthermore, channels that accommodate coordinating DMSO mol-
one DMSO molecule, one nitrate and two water molecules ecules, water molecules as well as the non-coordinating
were found in the unit cell but do not coordinate to the molecules of DMSO and nitrate (Figure 3).
bismuth atom. The infrared spectrum of [Bi(C18H14P(O)
Thermogravimetric analysis under nitrogen shows a
SO3)2(DMSO)3](NO3)‧DMSO‧2H2O in the solid state con- mass loss within three distinct steps. Up to 120°C, a mass
firms the coordination behavior determined by single- loss of 2.7% is observed which is assigned to the loss of
crystal X-ray diffraction. A strong absorption band at 1132 two water molecules (calc. 2.7%). The next step shows a
cm-1 shows the phosphine oxide coordination to bismuth. mass loss of 23.2% up to 300°C which is caused by the
The coordination of the sulfonate groups is demonstrated loss of four DMSO molecules (calc. 23.4%). Up to 800°C,
by absorption bands at 1030 cm-1 (νas(SO2)) and 1262 cm-1 a weight loss of 53.2% is noticed within one step. This is
(νs(SO2)), and the absorption band at 922 cm-1 represents assigned to the decomposition of nitrate and the coor-
the νS=O stretching vibration of coordinated DMSO mol- dinated organic ligands. Powder X-ray diffraction of the
ecules. A broad and weak absorption band at 3393 cm-1 final product shows the formation of elemental bismuth
shows the presence of water molecules that are not (ICDD 00-044-1246) and bismuth phosphate (ICDD
01-074-1635).
In conclusion, we have shown that the reaction of
[Bi6O4(OH)4](NO3)6‧H2O with 2-(diphenylphosphino)ben-
zenesulfonic acid in DMSO results in the oxidation of
phosphine to the corresponding phosphine oxide and,
subsequently, in the degradation of the hexanuclear
bismuth oxido cluster to give mononuclear [Bi(C18H14P(O)
SO3)2(DMSO)3](NO3)‧DMSO‧2H2O in 71% yield. Previously,
we have demonstrated that the hexanuclear bismuth oxido
cluster might be used as a starting material to produce
nanoscaled bismuth oxido clusters from DMSO solution.
Figure 2ꢀOxygen coordination environment of the bismuth atom in
However, in the presence of strongly coordinating chelate
the title compound. Symmetry transformations used: A=x, 0.5-y, z.
ligands, cluster degradation might be observed as shown
here.
Atomic positions of O2 and O3 are slightly disordered and have an
occupation factor of 0.5 (Bi(1)–O(2′): 2.74(2) Å; Bi1–O(3′): 2.88(2) Å).
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138ꢀ ꢀM. Schlesinger et al.: Synthesis and structure of a bismuth sulfonate
Figure 3ꢀView along [100]-axis of [Bi(C18H14P(O)SO3)2(DMSO)3](NO3)‧DMSO‧2H2O. H atoms are omitted for clarity.
Pfaltz, 2005). Sulfuric acid (819 mg, 2.39 mmol) was added to a
Experimental
solution of [Bi6O4(OH)4](NO3)6‧H2O (500 mg, 0.28 mmol) in DMSO at
80°C. The reaction mixture was stirred for 4 h and then cooled to
ambient temperature. Slow evaporation of the solvent over a peri-
od of 2 months gave [Bi(C18H14P(O)SO3)2(DMSO)3](NO3)‧DMSO‧2H2O
as colorless crystals with a yield of 1.13 g (71%). M.p. 103–104°C.
CHN: C44H56BiNO17P2S6; C 39.2 (calc. 39.6), H 4.4 (4.2), N 1.2 (1.1) %.
General
1H and 31P{1H}-NMR spectra were recorded on a Bruker spectrom-
eter (Advance III 500; 500 MHz) (Bruker Corporation, Billerica,
MA, USA) at room temperature. Attenuated total reflection infrared
spectra were recorded using a Spectromat FTS-165 spectrometer
(Bremen, Germany). Thermogravimetric experiments were performed
on a METTLER-TOLEDO GmbH (Postfach, Gießen, Germany) TGA/
DSC1 1100 system with a UMX1 balance. Melting points were deter-
mined on a Büchi Labortechnik GmbH (Essen, Germany) melting
apparatus (Melting Point B-540) and are uncorrected. The data set
for the single-crystal X-ray diffraction study was collected with Mo
Kα radiation (0.71073 Å) on an Oxford Gemini S diffractometer (Agi-
lent Technologies Sales & Services GmbH & Co. KG, Life Sciences &
Chemical Analysis, Waldbronn, Germany) at 110 K. All calculations
were performed using the SHELXTL program (Sheldrick, 1990). The
structures were solved by direct methods and refined by full-matrix
least squares on F2. The CCDC file 901691 contains the supplementa-
ry crystallographic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic Data Centre via
http://www.ccdc.cam.ac.uk/data_request/cif.
1
H-NMR (500.30 MHz, DMSO-d6): [δ] 8.14 (m, 1H), 7.77 (m, 1H),
7.67–7.47 (m, 11H), 7.22 (m, 1H), 3.36 (s, H2O). P{1H}-NMR (202.52
31
MHz, DMSO-d6): 39.4 ppm. IR [cm-1]: υ 3393 bw, 3050 w, 3015 w,
2971 w, 2920 w, 2852 w, 2361 m, 2344 m, 2168 w, 1587 w, 1484 w, 1435
m, 1347 m, 1262 m, 1182 w, 1132 s, 1123 s, 1090 s, 1068 s, 1030 s, 1007
s, 988 s, 951 s, 922 s, 832 w, 796 w, 779 m, 747 m, 729 m, 720 m, 693 s,
669 m, 610 m, 552 s, 538 m, 529 s, 484 w, 465 w, 442 m, 411 m. Crystal
data: C44H56BiNO17P2S6, M=1334.18, crystal size 0.2×0.2×0.2 mm³,
monoclinic, space group P21/m, Z=2, a=9.5436(1) Å, b=18.2414(2)
Å, c=15.1817(1) Å, β=90.434(1)°, V=2642.89(4) ų, Dc=1.677 g cm³,
F(000)=1344, μ(Mo-K ) =3.702 mm-1, T=110 K, 3.09<2 θ°<26.00°,
completeness to 2θ: 9α9.6% max./min. residual electron density:
3.191/-5.715 e/Å3. A total of 34,381 reflections collected, 5349 reflec-
tions were independent (Rint=0.0336). Final R1=0.0699 (I>2σ(I))
and wR2=0.1882 (all data).
Acknowledgments: We acknowledge Prof. Dr. Stefan
Spange for access to the ATR-IR instrument; Janine
Fritzsch and Natalia Rüffer for performing CHN analyses
and thermogravimetric analyses, respectively; and the
Deutsche Forschungsgemeinschaft (SPP1415) for financial
support.
Synthesis of [Bi(C H14P(O)SO3)2(DMSO)3]
(NO3)‧DMSO‧2H2O18
The starting material 2-(diphenylphosphino)benzenesulfonic acid
was synthesized according to a literature procedure (Schultz and Received September 24, 2012; accepted October 24, 2012
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ꢀ139
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