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Main Group Metal Chemistry

Editor-in-Chief: Jurkschat, Klaus

Editorial Board: Atwood, David / Basu Baul, Tushar S. / Beckmann, Jens / Chandrasekhar, Vadepalli / Izod, Keith / Jones, Cameron / Karlov, Sergey S. / Mehring, Michael / Molloy, Kieran / Naseer, Muhammad Moazzam / Ramasami, Ponnadurai / Ruhlandt-Senge, Karin / Ruzicka, Ales / Saito, Masaichi / Sarazin, Yann / Tokitoh, Norihiro / Wagler, Jörg


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Volume 36, Issue 3-4

Issues

Et4N[NO3(SnClPh3)2(SnPh3NO3)]: a trinuclear organostannate complex and related derivatives

Tidiane Diop
  • Corresponding author
  • Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, UCAD-sénégal, B.P 5005, Dakar, Senegal
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/ Libasse Diop
  • Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, UCAD-sénégal, B.P 5005, Dakar, Senegal
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/ François Michaud
  • Service Commun d’Analyse par Diffraction Rayons X, Université de Bretagne Occidentale, 6 avenue Victor Le Gorgeu, CS93837, 29238 Brest Cedex 3, France
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/ José Domingos Ardisson
  • Centro de Desenvolvimento da Tecnologia Nuclear (CDTN), Servico de Nanotecnologia (SENAN), Laboratorio de Fisica Aplicada, Av. Antonio Carlos 6.627, Campus da UFMG, Pampulha, 31270-901 Belo Horizonte, MG, Brazil
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Published Online: 2013-06-18 | DOI: https://doi.org/10.1515/mgmc-2013-0009

Abstract

Four new di- and triorganonitrato stannate complexes and related derivatives have been synthesized and characterized by infrared and Mössbauer spectroscopy. The structure of Et4N[NO3(SnClPh3)2(SnPh3NO3)] (1) has been determined by single-crystal X-ray diffraction analysis. In the trinuclear organostannate complex, each SnIV atom is five-coordinated and adopts a trigonal-bipyramidal trans-OXSnC3 (X=O or Cl) geometry. The overall coordination environment of the SnIV atoms is trans-octahedral for 2 and 3 or cis-trigonal-bipyramidal for 4. In the related derivatives, the NO3- anions behave as monodentate ligands.

Keywords: di- and triorganonitrato stannate; Mössbauer; octahedral; trigonal-bipyramida; trinuclear

Introduction

The various applications of organotin(IV) compounds in many fields such as agriculture, medicine, antifouling paints, and wood preservatives are the main reasons several research groups are involved in the synthesis of new organotin(IV) compounds (Růžička et al., 2002; Thoonen et al., 2004; Basu et al., 2005; Hadjikakou and Hadjiliadis, 2009). Reports on structure determinations or spectroscopic characterizations of triphenyltin(IV) derivatives with mono- and polybasic oxyanions (XOmn-; X=Cr, 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). Some nitrato derivatives (Jurkschat et al., 2003a; García-Cuesta et al., 2004; Seward et al., 2007; Anjaneyulu et al., 2010; Hakimi et al., 2012) have also been reported. Our groups have published some articles dealing with SnMe3- and SnPh3-containing derivatives with mono- and polybasic oxyanions [SO42-, C2O42-, PhP(H)O2-, HAsO42-] (Sall et al., 1995; Diallo et al., 2009; Gueye et al., 2011; Diop et al., 2013). In this paper, we report on the reactions between tetraethylammonium nitrate (Et4NNO3) or dicyclohexylammonium nitrate (Cy2NH2NO3) and mixing triphenyltin(IV) chloride (SnPh3Cl) or SnR2Cl2 (R=Ph, Bu), which have yielded a trinuclear organostannate complex and related derivatives. The structure in the solid state of Et4N[NO3(SnClPh3)2(SnPh3NO3)] has been determined by single-crystal X-ray diffraction analysis. All compounds have been characterized by Mössbauer and infrared spectroscopy.

Results and discussion

Molecular structure and spectroscopic characterization of Et4N[NO3(SnClPh3)2(SnPh3NO3)] (1)

The reaction of triphenyltin chloride (Ph3SnCl) with Et4NNO3 in the molar ratio 3:2 provided the trinuclear organostannate complex Et4N[NO3(SnClPh3)2(SnPh3NO3)] (1) as a colorless crystalline material that shows good solubility in ethanol [Eq. (1)].

The trinuclear organostannate complex consists of a discrete [NO3(SnClPh3)2(SnPh3NO3)]- anion and a tetraethylammonium cation Et4N+ (Figure 1). The [NO3(SnClPh3)2(SnPh3NO3)]- anion consists of two crystallographic independent SnClPh3 moieties and one SnONO2Ph3 moiety that each show a distorted trigonal-bipyramidal environment as a result of their simultaneous coordination to the central nitrate anion. The axial positions are occupied by O(1), O(4) (Sn1), Cl(1), O(2) (Sn2), and Cl(2), O(3) (Sn3), whereas the equatorial positions are taken by the ipso carbon atoms of the corresponding phenyl substituents. The central nitrate anion is μ3-bridging to three SnPh3 moieties, and the second nitrate anion coordinates the Sn(1) atom in a monodentate mode. A similar arrangement has been observed in the crystal structure of poly[μ2-chlorido-nonamethyl-μ3-nitrato-tritin(IV)], [(CH3)3Sn]3NO3Cl, (Rehman et al., 2007) with a nitrate anion coordinated to three Sn atoms. The Sn-O distances are in the accepted range [Sn-O: 2.216(10) and 2.459(5) Å] and are shorter than the Sn-O distances in [Ph4P]+[(Ph2ClSn)2CH2.NO3]- [Sn-O: 2.510(5) and 2.545(5) Å] (Jurkschat et al., 2003b), which are very close to those observed in Et4NNO3.SnPh2Cl2 [Sn-O: 2.292(11) Å] (Diop et al., 2011). The sum of the O-N(1)-O angles subtended at NO3- μ3-bridging [119.7° (6), 121.0° (6), and 119.3° (6)] is 360°, reflecting its trigonal-planar geometry. The C-N(70)-C angles of the cation are close to 109°, in agreement with the expected sp3 hybridization. Between the Et4N+ cations and the [NO3(SnClPh3)2(SnPh3NO3)]- anion, the interactions are mainly of electrostatic nature. The infrared (IR) spectrum of the complex in the 4000–400 cm-1 region shows the presence of bands due to the nitrate ring vibrations at 1070 cm-1 (s) and 1061 cm-1 (s), (ν1NO3); 1334 cm-1 (vs), 1362 cm-1 (vs), and 1392 cm-1 (vs) (ν3 NO3-). The presence of two bands of ν1NO3- reflects the two types of nitrates.

Molecular structure of Et4N[NO3(SnClPh3)2(SnPh3NO3)] (1) showing the labeling scheme (the hydrogen atoms have been omitted for clarity). Symmetry codes: (′) x, y, z (′′) -x, -y, -z; displacement ellipsoids are drawn at the 50% probability level.
Figure 1

Molecular structure of Et4N[NO3(SnClPh3)2(SnPh3NO3)] (1) showing the labeling scheme (the hydrogen atoms have been omitted for clarity). Symmetry codes: (′) x, y, z (′′) -x, -y, -z; displacement ellipsoids are drawn at the 50% probability level.

Selected bond distances (Å)

Sn(1)-O(4) 2.216(10); Sn(1)-O(1) 2.459(5); C(19)-Sn(2) 2.128(5); C(31A)-Sn(2) 2.188(12); Sn(2)-O(2) 2.502(5); Sn(2)-Cl(1) 2.512(4); C(37)-Sn(3) 2.134(5); C(43)-Sn(3) 2.125(4); C(49A)-Sn(3) 2.045(11); Sn(3)-Cl(2) 2.453(3); N(1)-O(2) 1.242(7); N(1)-O(1) 1.248(7); N(1)-O(3) 1.251(7); N(2)-O(4) 1.081(9); N(2)-O(5) 1.270(10); N(2)-O(6) 1.296(10); N(70)-C(77)#1 1.492(15); N(70)-C(71)#1 1.500(14); N(70)-C(73)#1 1.513(15).

Selected bond angles (°)

C(7B)-Sn(1)-C(1A) 119.8(6); C(1B)-Sn(1)-C(7A) 123.9(6); C(13)-Sn(1)-C(7A) 121.7(5); C(1A)-Sn(1)-C(7A) 116.5(6); C(7B)-Sn(1)-O(4) 96.8(5); O(4)-Sn(1)-O(1) 171.5(3); C(25A)-Sn(2)-C(31B) 117.1(8); C(25A)-Sn(2)-C(19) 116.8(5); C(31B)-Sn(2)-C(19) 124.2(5); C(25A)-Sn(2)-C(31A) 123.2(7); (49A)-Sn(3)-C(43) 122.9(5); O(2)-N(1)-O(1) 119.7(6); O(2)-N(1)-O(3) 121.0(6); O(1)-N(1)-O(3) 119.3(6); N(1)-O(1)-Sn(1) 125.4(4); N(1)-O(2)-Sn(2) 122.0(4); O(4)-N(2)-O(5) 125.3(11); O(4)-N(2)-O(6) 122.8(10); O(5)-N(2)-O(6) 111.8(10); N(2)-O(4)-Sn(1) 117.6(8); C(77)-N(70)-C(71) 110.1(12); C(77)-N(70)-C(73) 113.0(12); C(71)-N(70)-C(73) 112.9(11); C(77)-N(70)-C(75) 109.1(12).

A and B refer to the disorder of the molecular structure at the temperature measured.

Spectroscopic characterization of (Cy2NH2)4Cl2SnBu2(NO3)4 (2)

Methanolic solutions containing Cy2NH2NO3 and SnBu2Cl2 were mixed and stirred at room temperature for more than 1 h. The solution was allowed to evaporate to give powder of the title compound [Eq. (2)].

In comparison with the data reported for other nitrato adducts or derivatives (Addison et al., 1967; Nakamoto, 1997), we suggest the following IR band assignments to be made for the compound. The bands located at 1061 cm-1 (s,9ν1NO3), 1335 cm-1 (vs), and 1370 cm-1 (vs), (ν3NO3) are assigned to the vibrations of the NO3 groups.

The absence of νsSnBu2 in the IR spectrum indicates the n-Bu substituents to be trans. The Mössbauer spectrum of compound 2 shows a slightly asymmetric quadrupole split doublet with an isomer shift value (1.20 mm-1) in the normal range for a diorganotin(IV) derivative (Davies and Smith, 1982). The value of the quadrupole splitting (3.78 mm/s) is consistent with a trans hexacoordinated SnBu2moiety (Scheme 1) according to Bancroft and Platt (1972). These [SnBu2(NO3)4]2-, including the Cl atom, anions are then connected by the cation through NH⋯O hydrogen bonds responsible for the strong IR absorptions at 3340 and 3215 cm-1.

Suggested structure for (Cy2NH2)4Cl2SnBu2(NO3)4.
Scheme 1

Suggested structure for (Cy2NH2)4Cl2SnBu2(NO3)4.

Spectroscopic characterization of (Cy2NH2)2SnPh2Cl2(NO3)2(3)

The title compound, (Cy2NH2)2SnPh2Cl2(NO3)2 (3), was prepared by the condensation reaction of diphenyltin(IV) dichloride with Cy2NH2NO3 in a 1:2 molar ratio [Eq. (3)].

In the IR spectrum, the bands located at 1060 (s, ν1NO3), 1334, and 1375 (vs, ν3NO3) cm-1 are assigned to the stretching vibrations of the NO3 groups. The value of the quadrupole splitting of (3) (QS=3.57 mm/s) is consistent with the presence of a trans hexacoordinated SnPh2 group according to Bancroft and Platt (1972). The suggested structure for (3) consists of a trans-octahedral geometry around the SnIV atom (Scheme 2). The dicyclohexylammonium cation connects adjacent anionic [SnPh2(NO3)2Cl2]2- layers through N-H⋯O hydrogen bonding into a three-dimensional network structure.

Suggested structure for (Cy2NH2)2SnPh2Cl2(NO3)2.
Scheme 2

Suggested structure for (Cy2NH2)2SnPh2Cl2(NO3)2.

Spectroscopic characterization of (Cy2NH2)2ClSnPh2(NO3)3 (4)

(Cy2NH2)2ClSnPh2(NO3)3 (4) has been prepared by allowing Cy2NH2NO3 to react with diphenyltin dichloride, Ph2SnCl2, in methanol in the molar ratio 1:3 [Eq. (4)] (Scheme 3).

Suggested structure for (Cy2NH2)2ClSnPh2(NO3)3.
Scheme 3

Suggested structure for (Cy2NH2)2ClSnPh2(NO3)3.

The value of the quadrupole splitting (QS=3.07 mm/s) is consistent with a cis-trigonal-bipyramidal coordinated SnPh2 residue according to Bancroft and Platt (1972). The overall coordination environment of the SnIV atom is trigonal-bipyramidal defined by two phenyl C atoms in cis positions and three nitrate O atoms. The dicyclohexylammonium cation connects adjacent anionic [SnPh2(NO3)3]- layers through N-H⋯O hydrogen bonding into a three-dimensional network structure. The Cl atom can be involving in the hydrogen bonds network of supramolecular architecture.

Experimental

Materials and spectroscopic methods

SnPh2Cl2, SnBu2Cl2, SnPh3Cl, AgNO3, Et4NCl, HNO3, and Cy2NH were purchased from Aldrich or Merck Chemical Company and used without further purification.

The infrared spectra were recorded at the laboratory of control medicine (Dakar) by means 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-acceleration spectrometer moving a CaSnO3 source at room temperature. The samples were analyzed at liquid N2 temperature, and the isomer shift values are given with respect to that source. All the Mössbauer spectra were computer-fitted assuming Lorentzian lineshapes. Mössbauer parameters are given in mm/s (abbreviations: QS, quadrupole splitting; IS, isomer shift).

Synthesis of ligands

Et4NNO3 (L1) was obtained on mixing AgNO3 (0.50 g, 2.95 mmol) with tetraethylammonium chloride (Et4NCl) (0.82 g, 2.95 mmol) both in water and filtering off the AgCl precipitate (Sall et al., 1995).

Cy2NH2NO3 (L2) was obtained as a precipitate on mixing an aqueous solution of Cy2NH with NO3H in 1:1 ratio. Analytical data: % found (% calc. for ligand): % C, 58.76 (58.99); % H, 9.56 (9.90); % N, 11.00 (11.47).

Synthesis of Et4N[NO3(SnClPh3)2 (SnPh3NO3)](1)

Regular crystals of Et4N[NO3(SnClPh3)2(SnPh3NO3)] suitable for X-ray work were obtained after a slow solvent evaporation of the solution obtained on SnPh3Cl (0.23 g, 0.6 mmol) with Et4NNO3 (0.12 g, 0.40 mmol) in methanol in 3:2 ratio [melting point (mp), +260°C; yield, 82%].

Analytical data: [% found (% calc.) for C62H65Cl2N3O6Sn3, 1375.14 g]: % C: 54.32 (54.15); % H: 4.34 (4.76); % N: 2.95 (3.06). IR (cm-1, KBr): 3078 m (ν CH), 1070 s, and 1061 s (ν1NO3); 1334 vs, 1362 vs, and 1392 vs (ν3NO3).

X-ray crystallographic data of Et4N[NO3(SnClPh3)2(SnPh3NO3)] (1)

A crystal of approximate dimensions 0.13 mm×0.08 mm×0.07 mm was used for data collection. Data were collected at 298(2) K using Mo-kα radiation (λ=0.71073 Å).

Refinement of F2 against ALL reflections

The weighted R factor wR and goodness of fit S are based on F2, and conventional R factors R are based on F, with F set to zero for negative F2. The threshold expression of F2>2σ(F2) is used only for calculating R factors (gt), etc. and is not relevant to the choice of reflections for refinement. R factors based on F2 are statistically about twice as large as those based on F, and R factors based on all data will be even larger.

Data collection

CrysAlis CCD, Oxford Diffraction (2009); cell refinement: CrysAlis RED, Oxford Diffraction (2009); data reduction: CrysAlis RED, Oxford Diffraction; program used to solve structure: SHELXS97 (Sheldrick, 2008); program used to refine structure: SHELX97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004), PlATON (Spek, 1990, 1998), WinGX (Farrugia, 1999).

Crystal data and structure refinement

Empirical formula: C62H65Cl2N3O6Sn3; formula weight=1375.14; crystal system: triclinic; space group: P-1; a=14.0465(12) Å; b=15.0816(10) Å; c=16.0431(13) Å; α (°) = 85.611(6), β (o)=85.599(7), γ(°)=63.381(7); V3)=3026.0(4); Z=2; ρcalc (mg/m3)=1.509; μ(Mo-kα) (mm-1)=1.368; F(000): 1380; reflections collected: 23,179; independent reflections [R(int)]: 12,346 [0.062]; reflections observed (>2σ): 6014; absorption correction: semiempirical from equivalents; maximum, minimum transmission: 0.9103, 0.8422. Refinement method, full-matrix least squares on F2; goodness of fit, 0.825; final R indices [I>2σ(I)]: 0.0659, 0.1588; R indices (all data): 0.1502, 0.1832; largest difference peak and hole (eÅ3): 1.763, -0.672. The structure itself is highly disordered owing to the temperature measurement [298(2) K]. The crystallographic data for CCDC 859692 contain the supplementary crystallographic data for this paper.

Synthesis of (Cy2NH2)4Cl2SnBu2(NO3)4 (2)

(Cy2NH2)4Cl2SnBu2(NO3)4 (2) has been obtained by reacting (L2) (0.20 g, 0.80 mmol) with dibutyltin(IV) dichloride (SnBu2Cl2) (0.06 g, 0.20 mmol) in methanol. After a slow solvent evaporation a white powder was collected in the solvent (81%, mp 200°C).

Analytical data: [% found (% calc.) for C56H114Cl2O12Sn, 1280.7 g]: % C: 52.56 (52.50); % H: 8.92 (8.97); % N: 8.70 (8.75). IR (cm-1, KBr): 3340 s and 3215 s (ν NH2), 3160 m (ν NH), 3078 m (ν CH), 1061 s (ν1NO3); 1335 vs and 1370 vs (ν3NO3), 669w (νas SnBu2). Mössbauer data (mm/s): IS=1.20, QS=3.78.

Synthesis of (Cy2NH2)2SnPh2Cl2(NO3)2(3)

An ethanolic solution containing 0.10 g (0.4 mmol) of L2 and 0.07 g (0.2 mmol) of diphenyltin(IV) dichloride (SnPh2Cl2) was stirred at room temperature for more than 1 h. After a slow solvent evaporation of the solution a white powder was obtained (78%, mp 160°C).

Analytical data: [% found (% calc.) for C36H58Cl2N4O6Sn, 832.28 g]: % C: 52.00 (51.94); % H: 7.00 (7.02); % N: 6.70 (6.73). IR (cm-1, KBr): 3321 and 3000 m (ν NH2), 3160 m (ν NH), 3072 m (ν CH), 1060 s (ν1NO3); 1334 vs, and 1375 vs (ν3NO3). Mössbauer data (mm/s): IS=1.25, QS=3.57.

Synthesis of (Cy2NH2)2ClSnPh2(NO3)3 (4)

(Cy2NH2)2ClSnPh2(NO3)3 (4) has been obtained by reacting 0.10 g (0.4 mmol) of L2 with 0.05 g (0.13 mmol) of diphenyltin(IV) dichloride (SnPh2Cl2) in methanol. After a slow solvent evaporation a white powder was collected in the solvent (79%, mp 173°C).

Analytical data: [% found (% calc.) for C36H58ClN5O9Sn, 859.04 g]: % C: 50.23 (50.33); % H: 6.80 (6.81); % N: 8.40 (8.15). IR (cm-1, KBr): 3340 and 3215 m (ν NH2), 3160 m (ν NH), 3078 m (ν CH), 1061 s (ν1NO3); 1340 vs, and 1370 vs (ν3NO3). Mössbauer data (mm/s): IS=1.30, QS=3.07.

We thank Professor K. C. Molloy (University of Bath, UK) for performing the elemental analyses, and Djibril Fall (Cheikh Anta Diop University, Dakar , Senegal) for recording the infrared spectrum.

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About the article

Corresponding author: Tidiane Diop, Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop (UCAD), BP 5005, Dakar, Senegal


Received: 2013-02-20

Accepted: 2013-02-23

Published Online: 2013-06-18

Published in Print: 2013-07-01


Citation Information: Main Group Metal Chemistry, Volume 36, Issue 3-4, Pages 83–88, ISSN (Online) 2191-0219, ISSN (Print) 0792-1241, DOI: https://doi.org/10.1515/mgmc-2013-0009.

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