Synthesis, spectroscopic characterization and crystal and molecular structures of phenylphosphonato SnR3 (R=Ph, Me) derivatives

Article abstract of DOI:10.1515/mgmc-2012-0038

Four new phenylphosphonato SnR₃ (R=Ph, Me) derivatives have been synthesized and characterized by infrared and Moessbauer spectroscopy. The structure of catena-poly[PhPO₃HSnMe₃]_n has been determined by single-crystal X-ray diffraction analysis. The Sn^IV atoms are five-coordinated in all compounds, with the SnC₃O ₂ framework in a trans trigonal bipyramidal arrangement and the PhPO₃H^- anions being in axial positions. The molecular structure of [PhPO₃HSnMe₃]_n is arranged as a one-dimensional coordination polymer in which planar SnMe₃ groups are axially bridged by -O-P-O- linkages of the PhPO₃H^- ligand. Neighboring chains are linked via O-H...O hydrogen bond interactions, generating a layered structure. In the R₂NH ₂(PhPO₃H)₂SnR′₃ (R=Cy, Bu; R′=Ph, Me), the SnPh₃ or SnMe₃ residue is axially coordinated by two monodentate PhPO₃H^-. The role of the dialkylammonium cation, R₂NH₂⁺, is crucial in the lattice building via a hydrogen bond network. These hydrogen bonds contribute to the crystal stability and compactness and result in a three-dimensional arrangement. The aqua complex PhPO₃(SnPh ₃)₂·2H₂O has a discrete structure and the anion PhPO₃^2- behaves as a bidentate ligand.

Full text of DOI:10.1515/mgmc-2012-0038

ꢁꢁꢁꢂ
DOI 10.1515/mgmc-2012-0038ꢀ ꢀMain Group Met. Chem. 2013; 36(1-2): 29–34
Tidiane Diop*, Libasse Diop, Gabriele Kociok-Kohn, Kieran C. Molloy and
José Domingos Ardisson
Synthesis, spectroscopic characterization
and crystal and molecular structures of
phenylphosphonato SnR3 (R=Ph, Me) derivatives
Abstract: Four new phenylphosphonato SnR3 (R=Ph,
Me) derivatives have been synthesized and characterized
Introduction
by infrared and Mössbauer spectroscopy. The structure
Organotin(IV) complexes are extensively studied due to
of catena-poly[PhPO3HSnMe3]n has been determined by
their applications in industry as well as their biocidal
single-crystal X-ray diffraction analysis. The SnIV atoms
properties (Willem et al., 1997; Gielen, 2002; Davies
are five-coordinated in all compounds, with the SnC3O2
et al., 2008). Numerous studies on organotin(IV) com-
framework in a trans trigonal bipyramidal arrangement
plexes have been carried out in order to determine its
and the PhPO3H- anions being in axial positions. The
biological properties against bacteria, fungi and cancer
molecular structure of [PhPO3HSnMe3]n is arranged as a
cell lines (Teoh et al., 1997; Crouse et al., 2004). Reports
one-dimensional coordination polymer in which planar
on structure determinations or spectroscopic charac-
SnMe3 groups are axially bridged by -O-P-O- linkages of
terizations of trimethyl- and triphenyltin(IV) deriva-
the PhPO3H- ligand. Neighboring chains are linked via
tives with mono- and polybasic oxyanions (XOmn-; X=Cr,
…
O-H O hydrogen bond interactions, generating a layered
Se, S, As; m=3, 4; n=1, 2, 3) show that the oxyanions
behave mainly as polydentate ligands involving a one-
dimensional polymeric, bi- or tridimensional network
structure (Molloy et al., 1989; Diop et al., 2002; Diassé-
Sarr et al., 2004; Fall et al., 2010; Boye et al., 2012).
These triphenyltin(IV) or trimethyltin(IV) derivatives or
complexes exist as monomers or polymers with a five-
coordinated tin(IV) atom. Several papers dealing with
organotin(IV) chemistry and the coordinating ability
of phosphonates have been reported (Raymond et al.,
1992; Song et al., 2007; Chunlin et al., 2008; De Barros
et al., 2010; Shankar et al., 2011). The X-ray structure of a
tetragonal form of [SnMe3PhPO3H]n has been reported by
Molloy et al. (1981). Our group has conducted research
on SnMe3 and SnPh3 residues containing derivatives with
structure. In the R2NH2(PhPO3H)2SnR′3 (R=Cy, Bu; R′=Ph,
Me), the SnPh3 or SnMe3 residue is axially coordinated
by two monodentate PhPO3H-. The role of the dialkylam-
monium cation, R2NH2+, is crucial in the lattice building
via a hydrogen bond network. These hydrogen bonds con-
tribute to the crystal stability and compactness and result
in a three-dimensional arrangement. The aqua complex
.
PhPO3(SnPh3)2 2H2O has a discrete structure and the anion
PhPO32- behaves as a bidentate ligand.
Keywords: coordination polymer; phenylphosphonato
derivatives; tin; trigonal bipyramidal.
*Corresponding author: Tidiane Diop, Laboratoire de Chimie
Minérale et Analytique, Département de chimie, Faculté des
Sciences et Techniques, Université Cheikh Anta Diop, B.P 5005,
Dakar, Senegal, e-mail: tijchimia@yahoo.fr
Tidiane Diop and Libasse Diop: Laboratoire de Chimie Minérale
et Analytique, Département de chimie, Faculté des Sciences et
Techniques, Université Cheikh Anta Diop, Dakar, Senegal
Gabriele Kociok-Kohn and Kieran C. Molloy: Department of
Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK
José Domingos Ardisson: Centro de Desenvolvimento da Tecnologia
Nuclear (CDTN), Servico de Nanotecnologia (SENAN), Laboratorio
de Fisica Aplicada, Avenida Antonio Carlos, 6.627, Campus da
Universidade Federal de Minas Gerais, Pampulha, 31270-901 Belo
Horizonte, MG, Brazil
2-
2-
mono- and polybasic oxyanions (SO4 , C2O4 , PhP(H)O2-,
2-
HAsO4 ) (Diassé-Sarr et al., 2004; Diallo et al., 2009;
Diop et al., 2011; Gueye et al., 2011; Sow et al., 2012).
In this paper, we have initiated the study of interac-
tions between R2NH2PhPO3H (R=Bu, Cy) or PhPO(OH)2
and SnR3Cl (R=Ph, Me) or SnPh3OH that have yielded
the studied derivative and adducts, of which one struc-
ture has been determined by X-ray crystallography and
which have all been characterized by Mössbauer and
infrared spectroscopy.
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30ꢀ ꢀT. Diop et al.: Phenylphosphonato SnR3 derivatives and adducts
Results and discussion
larger [115.0(2)°]. The two P-O distances of the bridging O(1)-
P-O(3) moieties are also essentially equal, P-O(1) 1.507(3) Å
and P-O(3) 1.512(3) Å, indicating the presence of extensive
π delocalization of the P=O double bond. Although the
virtual linearity of the O(1)-Sn-O(3) bonds requires linearity
of the coordination polymer in the vicinity of the tin atoms,
the chains are bent through the tetrahedrally coordinated
phosphorus atoms of the phenylphosphonate ligand at
an O-P-O angle of 115.0(2)°. The parallel polymer adjacent
X-ray structure and spectroscopic
characterization of a monoclinic form of
catena-poly[PhPO3HSnMe3]n (1)
The structure of catena-poly[PhPO3HSnMe3]n consists of a
zigzag infinite chain with a trans-SnC3O2 framework, the
bidentate PhPO3H- moiety σ bonded to the SnMe3 group
(Figure 1). A similar chain arrangement around the tin atom
hasbeenobservedinthecrystalstructureofSnMe3O2P(OPh)2
(Newton et al., 1993) and {[(CH3)3Sn]4(O3PPh)2} n (Chunlin
et al., 2008). The Sn-O distances [2.182(3), 2.374(3) Å] and
the O(1)-Sn-O(3) angle of 171.47(12)° indicate unsymmetri-
cal coordination around the tin center and a significant
deviation from linearity when compared to the value in
the tetragonal form variety (Molloy et al., 1981) in which
Sn-O bond distances are 2.240(6) and 2.319(5) Å and the
O-Sn-O axial angle is 178.0°. The Sn-O distances of the
studied derivative, 2.216(11), 2.359(10) Å, compared to
the value in the tetragonal form, indicate the strengthen-
ing of one bond and the weakening of the other in the mon-
oclinic polymorph. These variations are accompanied by a
movement of the phenyl group of PhPO3H-, which moves
from a cis position (tetragonal form) to a trans position
(monoclinic form). In the title compound, the Sn-O bond
lengths are 2.182(3) and 2.374(3) Å, which are very close to
those observed in SnMe3MePO3H (Diop etꢀ al., 2002) [2.165(4)
and 2.434(4) Å] . The angles around the phosphorus atoms
are approximately tetrahedral except those including bridg-
ing oxygen atoms [O(1)-P-O(3)], which are significantly
…
chains are linked together by a network of O-H O hydrogen
…
…
bond interactions [O-H, 0.83 Å; H O, 1.76 Å; O(3) O(2), 2.61
Å] (Table 1) between the free O-H groups of the phenylphos-
phonato ligand and the coordinated oxygen, generating a
three-dimensional network (Figure 2).
The presence of a weak infrared band due to νsSnC3
at 515ꢁcm-1 for [SnMe3PhPO3H]n is an indication of almost
planar SnC3 groups (D3h) according to group theory. The
Mössbauer spectrum shows a slightly asymmetric quad-
rupole split doublet with an isomer shift (IS) value (1.34
mm/s) in the normal range for organotin(IV) derivatives
(Flinn et al., 1978). The quadrupole splitting value (3.78
mm/s) is consistent with the presence of trans coordinated
Me3Sn residues (Davies and Smith, 1982). The crystallo-
graphic study confirms the spectroscopic conclusions.
Selected bond distances (Å)
Sn-O(1) 2.182(3); Sn-O(3′) 2.374(3); Sn-C(2) 2.096(6);
Sn-C(3) 2.110(5); Sn-C(1) 2.123(6); P-O(1)1.507(3); P-O(3)
1.512(3); P-O(2) 1.563(4); P-C(4A) 1.744(11); P-C(4) 1.866(19);
O(2)-H(2) 0.85(2); O(3″)-Sn 2.374(3); C(4)-C(5) 1.3900; C(4)-
C(9) 1.3900; C(5)-C(6) 1.3900.
Selected bond angles (°)
O(1)-Sn-O(3′) 171.47(12); C(2)-Sn-C(3) 124.1(3); C(2)-Sn-C(1)
121.9(3); C(3)-Sn-C(1) 113.7(3); C(2)-Sn-O(1) 90.3(2); C(3)-Sn-
O(1) 90.40(19); C(1)-Sn-O(1) 94.82(18); C(2)-Sn-O(3′) 85.0(2);
C(3)-Sn-O(3′) 86.4(2); C(1)-Sn-O(3′) 93.71(18); O(1)-P-O(3)
115.0(2); O(1)-P-O(2) 107.7(2); O(3)-P-O(2) 109.1(2); O(1)-P-C(4)
109.1(7); O(3)-P-C(4)105.5(7); O(2)-P-C(4) 110.4(7); P-O(1)-Sn
141.4(2); P-O(2)-H(2) 116(5); P-O(3)-Sn#2131.30(18).
Table 1ꢁHydrogen bond geometry (Å, °).
Figure 1ꢀZigzag infinite chain of [SnMe3PhPO3H]n.
H atoms and the second component of the disordered phenyl ring
have been omitted for clarity. Symmetry codes: (’) 1/2-x, y-1/2,
1/2-z (″) x, y-1/2; displacement ellipsoids are drawn at the 50%
probability level.
…
…
…
…
D-H
A
D-H
H
A
D
A
D-H
A
O(2)-H(2)…O(2)
0.85
1.76(3)
2.610(5)
172(5)
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T. Diop et al.: Phenylphosphonato SnR3 derivatives and adductsꢀ
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...
Figure 2ꢀUnit cell of [SnMe3PhPO3H]n showing intermolecular P=O OH hydrogen bonds. The phenyl groups have been omitted for clarity.
X-ray crystallographic data of
[PhPO3HSnMe3]n
system, monoclinic; space group, P121/n1; a=11.0675(8)
Å, b=10.4180(6) Å, c=12.0670(8) Å; α=90°, β=103.584(3)°,
γ=90°; V=1352.42(15) Å3; Z=4; ρcalc=1.576 mg/m; μ
A crystal of approximate dimensions 0.20 mm×0.10 mm (Mo-Kα) =1.991 mm-1; F(000), 632; reflections collected,
×0.10ꢁmm was used for data collection. Program data were 11,929; independent reflections, [R(int)] 2986 [0.1207]; reflec-
collected on a Nonius Kappa CCD diffractometer at 150(2) tions observed, (>2σ) 1808; absorption correction: semi-
K using Mo-Kα radiation (λ=0.71073 Å); refinement was empirical from equivalents; maximum, minimum trans-
full-matrix least squares based on F2; the absorption cor- mission, 0.8258, 0.6916; refinement method, full-matrix
rection was semiempirical from equivalents. In the final least squares on F2; goodness of fit, 0.991; final R indices:
cycles of least-squares refinement all nonhydrogen atoms [I>2σ(I)]=0.0475, 0.0988; R indices (all data): 0.1041, 0.1185;
were allowed to vibrate anisotropically. The C-bound H largest difference peak and hole: 0.537, -1.853 eÅ3.
atoms were included in calculated positions and treated
as riding atoms: C-H=0.95 and 0.98 Å for CH and CH3 H
atoms, respectively, with Uiso(H)=K×Ueq(C), where K=1.2 Spectroscopic characterization
for CH H atoms, and K=1.5 for CH3 H atoms. However,
of Cy NH2(PhPO3H)2SnMe3 (2) and
Bu2N2H2(PhPO3H)2SnPh3 (3)
H binding to O(2) had to be restrained with O-H=0.82 Å. The
molecule includes a phenyl ligand disordered over two sites
in the ratio 40:60; C atoms in the rings have been restrained In comparison with the data reported for other phe-
to form an ideal hexagon, and C4 was refined isotropically. nylphosphonates adducts or derivatives (Adair et al.,
The following programs were used: SIR97 to solve 2003; Song et al., 2007; Chunlin et al., 2008; De Barros
structure (Altomare et al., 1999), SHELXL97 to refine et al., 2010; Shankar et al., 2011), we suggest the follow-
structure (Sheldrick, 2008), and ORTEP-3 for Windows for ing infrared band assignments to be made for the com-
molecular graphics (Farrugia, 1997, 1999). Crystallographic pound. The bands located at 1170 s, 1120ꢁs and 1083ꢁs for
data for the structural analysis have been deposited with Cy2NH2(PhPO3H)2SnMe3 (2) and 1135 s, 1102ꢁs and 1056ꢁs
the Cambridge Crystallographic Data Centre, CCDC No. for Bu2NH2(PhPO3H)2SnPh3 (3) are assigned to the stretch-
852507. Crystal data and structure refinement: empiri- ing vibrations of the PO3 groups. The bands at 948ꢁs cm-1
cal formula, C9H15O3PSn; formula weight, 320.87; crystal (2) and 947ꢁs cm-1 (3) are assigned to δPO3. The presence
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32ꢀ
ꢀT. Diop et al.: Phenylphosphonato SnR3 derivatives and adducts
R
O
R′
R′
P
H
N+
O
O
Sn
R′
O
OH
P
HO
R
H
Scheme 1:ꢁStructure of R2NH2(PhPO3H)2SnR′3 (R=Cy, Bu; R′=Me, Ph) (2 and 3).
of a Bruker FT-IR type spectrometer. The samples were prepared as
KBr pellets. Elemental analyses were performed at the University of
Bath (UK) using an Exeter Analytical CE440 analyzer. Infrared data are
given in cm-1 (abbreviations: vs, very strong; s, strong; m, medium; w,
weak). 119Sn Mössbauer spectra were obtained from a constant-acceler-
of νsSnC3 on the infrared spectra of (2) as a weak band is
an indication of D3h symmetry for the SnC3 residue. The
value of the quadrupole splitting (QS) of (3) (QS=3.57
mm/s) is consistent with the presence of a trans coordi-
nated SnPh3 group according to Bancroft and Platt (1972). ation spectrometer moving a CaSnO3 source at room temperature. The
samples were analyzed at liquid N2 temperature, and the IS values are
The suggested structure for (2) and (3) consists of a five-
given with respect to that source. All Mössbauer spectra were comput-
coordinate trigonal bipyramidal geometry around the
er-fitted assuming Lorentzian line shapes. Mössbauer parameters are
tin(IV) atom with two axial oxygen atoms of monodentate
given in mm/s.
PhPO3H- and three equatorial phenyl groups (Scheme 1).
N-H…O hydrogen bonds via the cation Bu2NH2+ or O-H…O
hydrogen bonds via hydrogenophenylphosphonate are
Synthesis of the ligands
forming a supramolecular architecture.
R2NH2R ′PO3H (R=Bu, Cy) was obtained as a white precipitate on
mixing an aqueous solution of R2NH (R=Bu, Cy; R′=Ph, Me) with
Spectroscopic characterization of
PhPO3H2 at 1:1 ratio. Analytical data: % found (% calc. for ligand):
Bu2NH2PhPO3H or C14H26NO3P (L1): % C=58.61 (58.52); % H=9.20 (9.12);
PhPO3(SnPh3)2·2H2O (4)
% N=4.80 (4.87). Cy2NH2PhPO3H or C18H30NO3P (L2): % C=63.66
(63.70); % H=9.00(8. 89); % N=4.17(4.13)
The QS value (=2.95 mm/s) of this dinuclear compound
is consistent with a dissymmetrical trans O2SnC3 ste-
reochemistry about the tin center according to Bancroft
and Platt (1972). This allows suggestion of a monomeric
structure, the environment around the tin center being
dissymmetrical trans trigonal bipyramidal, and the anion
PhPO32- bi-unidentate:
Synthesis of [PhPO3HSnMe3]n
A methanolic solution containing 0.2 g (0.69 mmol) of Bu2NH2Ph-
PO3H (L1) and 0.13 g (0.69 mmol) of trimethyltin(IV) chloride (SnMe3
Cl) was stirred at room temperature for more than 1 h. Afer 72ꢁh of
slow evaporation of the solution, colorless crystals of PhPO3HSnMe3
[yield: 62%; melting point (mp): 115°C] suitable for X-ray structure
determination were collected within the solvent. The powder ob-
tained afer complete solvent evaporation has the formula Bu2NH2Cl
according to its infrared spectrum.
Ph
Ph
Ph
Ph
H
Sn
H
O
O
O
Sn
O
O
The chemical substitution reaction is:
H
H
Ph
P
Ph
Bu2NH2PhPO2(OH)+SnMe3Cl→PhPO3HSnMe3+Bu2NH2Cl
Ph
Analytical data: % found (% calc. for C9H15O3PSn, 320.87
g/mol): % C, 33.69 (33.80); % H, 4.71 (4.02). Infrared data (cm-1): 1176
s, 1110 s, 1062 vs νPO3; 927ꢁs δPO3; 749ꢁm νPC 556ꢁs νasSnC3; 515ꢁw
νsSnC3. Mössbauer data (mm/s): IS=1.34, QS=3.78, Г (full width at
half-height)/2=0.43.
Experimental
Materials and spectroscopic methods
SnMe3Cl, SnPh3Cl, SnPh3OH, the PhPO(OH)2, and R2NH (R=Bu, Cy)
were purchased from Aldrich Chemical Company, Inc (product of
Synthesis of Cy2NH2(PhPO3H)2SnMe3
Germany) and used without further purification. The infrared spectra Cy2NH2(PhPO3H)2SnMe3 (B) has been obtained by reacting 0.25 g (0.73
were recorded at the laboratory of control medicine (Dakar) by means mmol) of L2 with 0.073 g (0.36 mmol) of trimethyltin(IV) chloride
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T. Diop et al.: Phenylphosphonato SnR3 derivatives and adductsꢀ
ꢀ33
(SnMe3Cl) in methanol. Afer a slow solvent evaporation, a white
powder was collected in the solvent (75%, mp 170°C).
The chemical substitution reaction is:
Analytical data: % found (% calcd. for C38H47NO6P2Sn, 795.19
g/mol): % C, 57.37 (57.45); % H: 5.92 (5.96); % N, 1.12 (2.76). Infrared
data (cm-1): 3287 vs, 2954 br, νNH2; 1282ꢁs νOH; 1135 s, 1102 vs νPO3;
947ꢁs νPC. Mössbauer data (mm/s): IS=1.25, QS=3.57, Г=0.85.
2Cy2NH2PhPO2(OH)+SnMe3Cl→Cy2NH2(PhPO3H)2SnMe3+Cy2NH2Cl
Analytical data: % found (% calc. for C27H45NO6P2Sn, 660.27
g/mol): % C, 48.88 (49.11); % H, 6.93 (6.87); % N, 2.23 (2.12). Infrared
data (cm-1): 3289 vs, 3227 s, 2759 br, νNH2; 1284ꢁs νOH; 1170 s, 1083 vs
νPO3; 948ꢁs νPC; 558ꢁs νasSnC3; 517ꢁw νsSnC3.
.
Synthesis of PhPO3(SnPh3)2 2H2O
The dinuclear compound was obtained by reacting 0.06 g (0.40 mmol)
of phenylphosphonic acid with 0.08 g (0.23 mmol) of triphenyltin(IV)
hydroxide (SnPh3OH) in methanol. Afer a slow solvent evaporation a
white powder was collected in the solvent (80%, mp 120°C).
The chemical substitution reaction is:
.
Synthesis of Bu2NH2(PhPO3H)2SnPh3
PhPO(OH)2+2SnPh3OH→PhPO3(SnPh3)2 2H2O
Analytical data: % calc. (% found for C42H39O5PSn2, 891.4
g/mol): % C, 56.54 (56.50); % H, 4.37 (4.31). Infrared data (cm-1):
1160 s, 1109 vs, 1009ꢁs νPO3; 928ꢁs δPO3; 746ꢁm νPC. Mössbauer data
(mm/s): IS=1.23, QS=2.95, Г=0.98 0 . 0 4 .
An ethanolic solution containing 0.30 g (1.04 mmol) of L1 and 0.20 g
(0.52 mmol) of triphenyltin(IV) chloride (SnPh3Cl) was stirred at room
temperature for more than 1 h. Afer a slow solvent evaporation of the
solution a white powder was obtained (89%, mp 187°C).
The chemical substitution reaction is:
Received July 21, 2012; accepted January 12, 2013; previously
published online February 16, 2013
2Bu2NH2PhPO2(OH)+SnPh3Cl→Bu2NH2(PhPO3H)2SnPh3+Bu2NH2Cl
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