Triorganotin Chlorides Research Articles

Synthesis, characterization, exploration of anti-cancer, anti-leishmanial, anti-microbial activities, pharmacokinetic and docking studies of Sn(IV) complexes

Six new triorganotin(IV) derivatives: [(C6H5)3Sn(C11H11N2O6)] (1), [(C6H11)3Sn(C11H11N2O6)] (2), [(C7H7)3Sn(C11H11N2O6)] (3), [(CH3)3Sn(C11H11N2O6)(C10H8N2)] (4), [(CH3)3Sn(C11H11N2O6)(C12H8N2)] (5), [(CH3)3Sn(C11H11N2O6)(C14H12N4)] (6) were designed and prepared by the reaction of sodium 3‐[(4‐methoxy‐2‐nitrophenyl)carbamoyl]propanoic acid with the corresponding triorganotin(IV) chlorides. Their synthesis was confirmed by 1H, 13C and 119Sn-NMR, percentage elemental constituents, FT-IR, and ESI-mass spectrometric techniques. The OH stretching vibration of the carboxylic moiety in the spectrum of the free acid was absent in that of the sodium salt (NaL) of the acid which proves its formation. Moreover, the appearance of Sn-C and Sn-O stretching vibrations in the spectra of complexes conform their formation. The antimicrobial activity of the investigated compounds explored good antimicrobial activity in comparison to the reference drugs. The tested compounds were also treated against H-157 and BHK-21 cancerous cell lines and possess good anticancer potential in comparison to the vincristine drug used as standard. So based on the activity results it is concluded that the synthesized complexes after positive in vivo and other clinical studies may be used for cancer treatment. The tested compounds exhibit good anti-leishmanial activity. The results of molecular docking performed against cancer death receptor BRCA2 (PDB# 1NOW) and Leishmania major Pteridine reductase 1 (PTR1) of Escherichia coli BL21 (PDB # 5L42) also verify the in vitro experimental results. Pharmacokinetic properties of the tested compounds such as drug-likeness, bioavailability score etc. were determined and most of them follow the Lipinski’s rule of 5.

Synthesis, characterization, and biological evaluation of eight new organotin(IV) complexes derived from (1R, 2S) ephedrinedithiocarbamate ligand

The synthesis of eight new organotin derivatives containing ephedrine-substituted dithiocarbamate ligands [R3Sn(ephedtc)] 2–5. 2: R = Me; 3: R = Bu; 4: R = Cy; 5: R = Ph and [R2Sn(ephdtc)2] 6–9. 6: R = Me; 7: R = Bu; 8: R = t-Bu; 9: R = Ph is reported. The complexes were obtained from sodium ephedrinedithiocarbamate [Na(ephedtc)] 1 and the corresponding tri-organotin(IV) chlorides, R3SnCl 2–5 or di-organotin(IV) dichlorides, R2SnCl26–9. They were characterized by elemental analysis, IR, and NMR spectroscopy (1H, 13C, and 119Sn). The infrared spectra (solid-state) suggest that the Sn(IV) is coordinated to the ligand ephedtc, through the two sulfur atoms in an anisobidentate coordination mode. In solution, the 119Sn NMR indicates the coordination numbers: tetracoordinated for 2–4, pentacoordinate for 5, and hexacoordinated for 6–9. The single-crystal X-ray diffraction analysis of 4 reveals an anisobidentate coordination mode with a trigonal bipyramid distorted geometry around the Sn(IV). All compounds except 2, show inhibition in at least one bacterial strain, and 7 and 9 have the best antibacterial activity, mainly in the clinically isolated strains.

Synthesis, structural characterization and antimicrobial activities of triorganotin(IV)azo-carboxylates derived from ortho/para-amino benzoic acids and β-naphthol

Triorganotin (IV) complexes 1–3 were synthesized by the reaction of azo-carboxylic acid viz. 2/4-(2-hydroxynaphthylazo)benzoic acids with appropriate triorganotin(IV) chlorides [R = Me (compounds 1 and 2) and Bu (compound 3)] in presence of triethyl amine base. The complexes were characterized by elemental analysis, IR and multinuclear (1H and 13C- and 119Sn)-NMR spectroscopy. The structures and mode of coordination around tin ions in the complexes were determined by single crystal X-ray crystallography. The complexes exhibit trigonal bipyramidal geometry around tin atoms where the base of the equatorial plane is being occupied by the three alkyl groups [Me or Bu] while the axial positions are occupied by carboxylate oxygen atoms in 2 and in case of 1 and 3, by carboxylate and phenoxide oxygen atoms, respectively. It has been found that, the crystal structure of 1 or 3 is a cyclic dimeric, whereas 2 exhibits a polymeric structure. The 119Sn NMR studies show that all complexes have four-coordinate structures indicating dissociation of these complexes in solution state. The complexes were also screened for their antimicrobial activity and the compound 3 was found to exhibit effective antimicrobial activity.

Novel organotin (IV) complexes derived from 4,4′‐oxybisbenzoic acid: synthesis, structure, in vitro cytostatic activity and binding interaction with BSA

Six novel organotin (IV) complexes, [(Me3Sn)2(H2O)2L] (1), [(R3Sn)2L]n (R = Me 2, R = n‐Bu 3), [(Ph3Sn)2L] (4), [Me2SnL]n (5), [(Me2Sn)2L(μ3‐O)]n (6) have been designed and synthesized by the reactions of 4,4′‐oxybisbenzoic acid (H2L) and triorganotin (IV) chloride or oxide. All the complexes have been characterized by elemental analysis, FT‐IR, NMR, ESI‐Mass, PXRD and X‐ray crystallography. The single crystal diffraction reveals that complexes 1 and 4 represent dinuclear tin monomers. Complexes 2 and 3 display 2D network structure and 2D corrugated framework respectively, which both contain tetranuclear 36‐membered macrocycles. Furthermore, 2D structures are linked into a 3D supramolecular structures through intermolecular C‐H···π interactions. Complex 5 shows 1D infinite helical chain and further constructs 3D ladder supramolecular architecture through additional Sn···O and C‐H···O intermolecular interactions. Complex 6 displays 1D infinite polymeric chain containing 28‐membered macrocyclic ring. Preliminarily in vitro cytostatic activity studies on cervical carcinoma cell lines (HeLa) and hepatocellular carcinoma cell lines (HepG‐2) by MTT assay for some complexes reveal that complexes 3 and 4 exhibit high cytostatic activity. Further, complexes 3 and 4 were selected to investigate interactions of bovine serum albumin (BSA) by fluorescence quenching spectra and synchronous fluorescence spectra, which indicates that the complexes could quench the intrinsic fluorescence of BSA in a static quenching process.

Structure and bonding in triorganotin chlorides: a perspective from energy decomposition analysis.

The Sn-Cl chemical bond of four organotin halides (Me3SnCl, Et3SnCl, Bu3SnCl, and Ph3SnCl) was studied by using relativistic density functional theory in combination with a quantitative energy decomposition analysis to explain the formation of charged species. The σ orbital is the dominant contributor to the stabilization of the Sn-Cl bond, and the π-orbital interactions also have a significant contribution to the stabilization of Ph3Sn+ cation when the aromatic groups are bonded to the tin atom. The aromaticity of the phenyl groups delocalizes the positive charge, donating electrons to tin atom by conjugation. Although Me3SnCl and Ph3SnCl are constituted by groups which the size of the substituents is different, the interaction energies obtained with the energy decomposition analysis present similar values, which also occur with the thermodynamic parameters. Graphical abstract Organotin compounds have widely studied as a potential antitumoral agent. The mechanism in triorganotin compounds includes the formation of cation species, R3Sn+. This article studies the influence of the R groups on the rupture of Sn-Cl bond using the fragment analysis and quantitative energy decomposition analysis.

Syntheses and crystal structures of three bis(triorganotin) benzenedicarboxylates

AbstractThree bis(triorganotin) benzenedicarboxylates, 1,n-C6H4(COOSnR3)2(n, R=3, C6H5C(CH3)2CH2,1; 4, C6H5C(CH3)2CH2,2; 4, C6H11-c,3), were synthesized by the reaction of 1,3 or 1,4-benzenedicarboxylic acid with triorganotin chlorides in the solution of CH3ONa-CH3OH and characterized by means of elemental analysis, Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) (1H,13C, and119Sn) spectra, and X-ray single-crystal diffraction. Compounds1–3are all di-nuclear tin complexes in which the carboxylate is monodentate and each tin atom possesses a distorted SnC3O tetrahedral geometry.

Organotin(IV) 4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazine-1-carbodithioates: Synthesis, characterization and biological activities

A series of organotin(IV) derivatives R3SnL (1–3), R2SnLCl (4–6) and R2SnL2 (7–9) (where R = Me, Bu, Ph and L = 4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazine-1-carbodithioate) were prepared from the reaction of 4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazine-1-carbodithioate (L-salt) with the corresponding triorganotin(IV) chlorides and diorganotin(IV) dichlorides. All compounds were characterized by FT-IR, 1H, 13C and 119Sn NMR spectroscopy. Dimethylstannyl bis(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazine-1-carbodithioate) (7) was also characterized in the solid state by single crystal x-ray diffraction, showing a distorted octahedral geometry. The diorganotin(IV) derivatives have shown significant antibacterial and antifungal activity and good cytotoxic activity against ovarian cancer cells with IC50 values greater or comparable to that of cisplatin.

Synthesis, Characterization, and Anticancer Activity of Organotin(IV) Complexes with Sodium 3-(1H-Indol-3-yl)propanoate

Six organotin(IV) complexes have been synthesized by refluxing sodium salt of 3-(1H-indol-3-yl)-propanoic acid with di- and triorganotin chlorides in 1: 1 and 2: 1 molar ratios, respectively. These complexes have been characterized by elemental analysis, IR, and 1H, 13C, and 119Sn NMR spectral data. DNA binding studies were performed by viscometric measurements and UV-Vis spectroscopy. Both techniques indicated an intercalation mode of interaction. Cytotoxic activity of the ligand salt and organotin(IV) complexes 1–6 was tested against human ovarian cell line A2780. Results of bioassay revealed that organotin derivatives were more active than anticancer drug cis-platin. Triorganotin(IV) compounds had higher cytotoxic activity than corresponding diorganotin(IV) complexes.

Synthesis, characterization, single crystal XRD and biological screenings of organotin(IV) derivatives with 4-(2-hydroxyethyl)piperazine-1-carbodithioic acid

Organotin(IV) thiocarboxylates R2SnL2 (R = Me: 1: Ph: 2)/R2(Cl)SnL (R = n-Bu: 3; Ph: 4)/R3SnL (R = Me: 5; n-Bu: 6; Ph: 7), where L = 4-(2-hydroxyethyl)piperazine-1-carbodithioate, have been synthesized by stirring together 1,2-hydroxyethylpiperazine and CS2 in methanol, and then refluxing with a di-/triorganotin chloride. The synthesized products have been characterized by various spectroscopic (IR, 1H NMR, 13C NMR, EI-MS) techniques and single crystal XRD. FT-IR data indicate bidentate binding of the ligand. The magnitude of 2J(119Sn–1H) demonstrated a skew trapezoidal environment around tin(IV) in 1, whereas the metal geometry in 5 was between distorted tetrahedral and trigonal bipyramidal in solution. 13C NMR revealed four- and five-coordinate environments in 6 and 7, respectively, in non-coordinating solvent. EI-MS data agreed very well with the structural skeleton of the products. Single crystal XRD study has shown skew trapezoidal- and trigonal-bipyramidal Sn(IV) in 1 and 7, respectively. Compound 6 interacted with salmon sperm DNA (SS-DNA) with significant hypochromic effect and an intercalating mode of binding. Diorganotin(IV) derivatives (2 and 3) generally exhibited poor antibacterial/antifungal potential as compared to their trialkyltin(IV)/triaryltin(IV) counterparts (5 and 6). The in vitro hemolytic activities show that average lysis of human red blood cells caused by 1–7 was significantly lower compared to triton X-100 (positive control, 100% lysis) and not very much higher than PBS (negative control, 0% lysis).

Synthesis, characterisation and anti-diabetic activities of triorganotin(IV) azo-carboxylates derived from amino benzoic acids and resorcinol: Crystal structure and topological study of a 48 membered macrocyclic-tetrameric trimethyltin(IV) complex

Triorganotin(IV) complexes of azo-carboxylic acids derived from amino benzoic acids and resorcinol were synthesized by the reaction of 2/4-(2,4-dihydroxy-phenylazo)-benzoic acids with appropriate triorganotin(IV) chlorides [R=Me (1 and 3), Ph (2 and 4) and Bu (5)] in presence of triethylamine. The characterisation of the complexes was accomplished by elemental analyses, UV, IR and multinuclear (1H, 13C and 119Sn) NMR spectroscopy. Structure of compound 3 was established by X-ray crystal structure analysis. X-ray crystal structure of 3 revealed that the compound exhibits a 48 membered macrocyclic-tetrameric structure with trigonal bipyramidal geometry around the tin atoms in which the three methyl groups occupy the equatorial positions while the apical positions are being occupied by the oxygen atom of carboxylate group of one ligand and the phenoxide oxygen atom of another ligand. The coordination network in 3 has also been analysed from the topological viewpoint. All the complexes display a sharp singlet 119Sn resonance in the range specified for the four coordinate structures suggesting that complexes have tetrahedral structures in solution. The five coordinate structure of the complexes in solid state dissociated into monomeric species with four coordinate structures in solution. Anti-diabetic activities of the complexes were studied and the results showed that the compounds 2, 3 and 4 exhibited effective activity even higher than the standard compound.

Synthesis, spectral, DFT, and semi-empirical study of trimetallic complexes with pyrazole-3,5-dicarboxylic acid containing Sn(IV) and Hg(II)

Trimetallic compounds have been synthesized by treating pyrazole-3,5-dicarboxylic acid with CS2, di-, and triorganotin(IV) chlorides and HgCl2 under reflux. The complexes have been characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy. Dipole moments and charges were calculated by the semi-empirical method. Two complexes were studied by DFT (BLYP/3-21G, B3LYP-3-21G) and semiempirical methods (PM3, PM6, MNDO, AM1, ab initio). IR data indicated that Sn was attached to oxygen of the carboxylic groups in a bidentate manner and adopted trigonal bipyramidal geometry. Hg was bonded to both S atoms of a ligand and exhibited square planner geometry in solid state. NMR data confirmed the four coordinated geometry of compounds in solutions.

Multinuclear NMR and crystallographic studies of triorganotin valproates and their in vitro antifungal activities

The reactions of triorganotin chlorides and sodium valproate, Na(OVp), yielded three triorganotin valproates [{SnMe3(OVp)}n] (1), [{SnBu3(OVp)}n] (2) and [SnPh3(OVp)] (3). All complexes have been authenticated in terms of infrared, 1H and 13C NMR, and solution- and solid-state 119Sn NMR, 119Sn Mössbauer and X-ray crystallography. The 119Sn NMR experiments provided important informations concerning the structures of (1)–(3) in solution and in the solid state. The X-ray experiments revealed the double-polymeric chain of complex (1), in which the geometry at the Sn(IV) is trigonal bipyramidal with intermolecular valproate bridges. The structure of complex (3) was re-determined and the new data show the tin cation at the centre of a distorted trigonal bipyramid, and not coordinated by four electron donating groups. The biological activity of all derivatives has been screened in terms of IC50 (μmolL−1) against C. albicans (ATCC 18804), C. tropicalis (ATCC 750), C. glabrata (ATCC 90030), C. parapsilosis (ATCC 22019), C. lusitaniae (CBS 6936) and C. dubliniensis (clinical isolate 28). Complex (3) exhibited the best biocide activity.

Synthesis, characterization, crystal structures and in vitro antimicrobial activities of triorganotin(IV) complexes of azo-dicarboxylates

Triorganotin(IV) complexes (R=n-butyl, phenyl and methyl) of azo-dicarboxylates were synthesized by reacting bis-tri-n-butyltin(IV) oxide with (E)-5-((2-carboxyphenyl)diazenyl)-2-hydroxy benzoic acid (L1HH′) [compound 1] and tri-organotin(IV) chlorides [R=Ph, Me] with either sodium salt of (E)-5-((2-carboxyphenyl)diazenyl)-2-hydroxy benzoic acid (L1Na) [compounds 2 and 3] or sodium salt of (E)-5-((4-carboxyphenyl)diazenyl)-2-hydroxy benzoic acid (L2Na) [compounds 4 and 5]. The complexes were characterized by elemental analysis, UV, IR and NMR-spectroscopy. NMR studies of the triorganotin(IV) complexes indicate that the complexes adopt 4-coordinate quasi tetrahedral geometry in solution state. The structures of complexes 1 and 3 in solid state were characterized by X-ray crystallography. The crystal structure analyses show that the complexes have polymeric structures with distorted trigonal bipyramidal geometry around tin atoms. Classical intra-molecular hydrogen bonds O—H⋯O have been observed in both the complexes. In-vitro antimicrobial activities of the complexes were also screened against various microbes and found to be effective.

Synthetic, Structural, and Spectroscopic Studies of Sterically Crowded Tin–Chalcogen Acenaphthenes

A series of sterically encumbered peri-substituted acenaphthenes have been prepared containing chalcogen and tin moieties at the close 5,6-positions (Acenap[SnPh3][ER], Acenap = acenaphthene-5,6-diyl, ER = SPh (1), SePh (2), TePh (3), SEt (4); Acenap[SnPh2Cl][EPh], E = S (5), Se (6); Acenap[SnBu2Cl][ER], ER = SPh(7), SePh (8), SEt (9)). Two geminally bis(peri-substituted) derivatives ({Acenap[SPh2]}2SnX2, X = Cl (10), Ph (11)) have also been prepared, along with the bromo–sulfur derivative Acenap(Br)(SEt) (15). All 11 chalcogen–tin compounds align a Sn–CPh/Sn–Cl bond along the mean acenaphthene plane and position a chalcogen lone pair in close proximity to the electropositive tin center, promoting the formation of a weakly attractive intramolecular donor–acceptor E···Sn–CPh/E···Sn–Cl 3c-4e type interaction. The extent of E→Sn bonding was investigated by X-ray crystallography and solution-state NMR and was found to be more prevalent in triorganotin chlorides 5–9 in comparison with triphenyltin derivatives 1–4. The increased Lewis acidity of the tin center resulting from coordination of a highly electronegative chlorine atom was found to greatly enhance the lp(E)−σ*(Sn–Y) donor–acceptor 3c-4e type interaction, with substantially shorter E–Sn peri distances observed in the solid state for triorganotin chlorides 5–9 (∼75% ∑rvdW) and significant 1J(119Sn,77Se) spin–spin coupling constants (SSCCs) observed for 6 (163 Hz) and 8 (143 Hz) in comparison to that for the triphenyltin derivative 2 (68 Hz). Similar observations were observed for geminally bis(peri-substituted) derivatives 10 and 11.

Sterically Restricted Tin Phosphines, Stabilized by Weak Intramolecular Donor–Acceptor Interactions

Four related sterically restricted pen-substituted acenaphthenes have been prepared containing mixed tin phosphorus moieties in the proximal 5,6-positions (Acenap[SnR3][(PPr2)-Pr-i]; Acenap = acenaphthene-5,6-diyl; R-3 = Ph-3 (1), Ph2Cl (2), Me2Cl (3), Bu2Cl (4)). The degree of intramolecular P-Sn bonding within the series was investigated by X-ray crystallography, solution and solid-state NMR spectroscopy, and density functional theory (DFT/B3LYP/SBKJC/PCM) calculations. All members of the series adopt a conformation such that the phosphorus lone pair is located directly opposite the tin center, promoting an intramolecular donor acceptor P -> Sn type interaction. The extent of covalent bonding between Sn and P is found to be much greater in triorganotin chlorides 2-4 in comparison with the triphenyl derivative 1. Coordination of a highly electronegative chlorine atom naturally increases the Lewis acidity of the tin center, enhancing the Ip(P)-sigma*(Sn-Y) donor acceptor 3c-4e type interaction, as indicated by conspicuously short Sn-P peri distances and significant (1)J(P-31,Sn-119) spin spin coupling constants (SSCCs) in the range 740-754 Hz. Evidence supporting the presence of this interaction was also found in solid-state NMR spectra of some of the compounds which exhibit an indirect spin spin coupling on the same order of magnitude as observed in solution. DFT calculations confirm the increased covalent bonding between P and Sn in 2-4, with notable WBIs of ca. 0.35 obtained, in comparison to 0.1 in 1.

Synthesis and structural elucidation of bioactive triorganotin(IV) derivatives of sodium deoxycholate

Trimethyl (1), tributyl (2), and triphenyl tin (3) derivatives of sodium (R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate (sodium deoxycholate) were synthesized by refluxing sodium deoxycholate with the corresponding triorganotin(IV) chloride in 1 : 1 M ratio. All the three compounds were characterized by elemental analysis, infrared spectroscopy, 1H, 13C, 119Sn NMR, and X-ray diffraction studies. From FT-IR spectra, Δν values proposed bridging or chelating behavior of the ligand. The three compounds gave a trigonal bipyramidal geometry in the solid state and tetrahedral geometry in solution. Single crystal of 1 showed polymeric trigonal bipyramidal geometry. Synthesized compounds obtained were screened for their antimicrobial and antitumor activities against A2780 cell line. Results revealed that only 2 showed significant antibacterial activity. However, all the three compounds exhibited promising antifungal and anticancer activities.

Design, spectral characterization, anti-tumor and anti-inflammatory activity of triorganotin(IV) hydroxycarboxylates, apoptosis inducers: In vitro assessment of induction of apoptosis by enzyme, DNA-fragmentation, acridine orange and comet assays

Interaction of triorganotin(IV) chlorides with sodium salt of hydroxycarboxylic acids results in the formation of triorganotin(IV) hydroxycarboxylates, R3Sn(L) [R=Me, n-Bu and Ph; L=anion of glucuronic (HGlu), gallic (HGal) and mandelic (HMal) acid]. They exhibit trigonal–bipyramidal geometry which is well supported by elemental analysis, IR, 1H, 13C, 119Sn NMR and ESI-MS spectral data. Triorganotin(IV) hydroxycarboxylates have been screened in vitro against five cancer cell lines of human origin viz. MCF-7, HEK-293, PC-3, HCT-15 and HepG-2. Title complexes are found to be cytotoxic to mildly cytotoxic, and exhibited IC50 values in the range 4–30μg/mL. The results of enzyme assays viz. glutathione reductase, glutathione peroxidase, total glutathione content and lipid peroxidase assay on MCF-7 cells indicate that the reactive oxygen species generated in the cancer cells by triorganotin(IV) hydroxycarboxylates is responsible for cell death. Marginal increase of lactate dehydrogenase suggests that necrosis is also occurring to a small extent. DNA (deoxyribonucleic acid) fragmentation assay, acridine orange assay and comet assay clearly support that the cell death is mainly due to apoptosis. The results obtained for the in vivo anti-inflammatory activity (% inhibition) and toxicity (LD50 in mg/kg) suggested that the complexes have low toxicity and good anti-inflammatory activity.

Synthesis, Spectroscopic study & Biological Activity Of Some Organotin(Iv) Derivatives Of (2e)-N-Methyl-(2-Oxo 1,2diphenylethylidne)Hydrazinecarbothioamide

Some di-and triorganotin(IV) derivatives of (2E)-N-methyl-(2 oxo1,2diphenylethylidne)hydrazinecarbothioamide synthesised by the reactions of the corresponding di and triorganotin(IV) chlorides with the sodium salt of (2E)-N-methyl-(2- oxo1,2diphenylethylidne)hydrazinecarbothioamide in different molar ratios. These derivatives have been characterized by elemental analyses ,molecular weights, conductivity measurements and spectral(IR, 1 H, 13 C and 119 Sn NMR) studies.

Assembly of triorganotin chloride with selenite ligands to macrocyclic, zigzag, helical, and linear structures: syntheses, characterizations, and crystal structures of [R3Sn(O2SeC6H4-4-Et)] n and [R3Sn(O2SeC6H4-2-Et)] n (R = Me, C6H5) complexes

Four new triorganotin(IV) complexes, [R3Sn(O2SeC6H4-4-Et)]4 (R = Me 1), [R3Sn(O2SeC6H4-4-Et)] n (R = Ph 2), [R3Sn(O2SeC6H4-2-Et)] n (R = Me 3; Ph 4) have been synthesized by the treatment of 4-ethylbenzeneseleninic acid, 2-ethylbenzeneseleninic acid, and the corresponding triorganotin(IV) chloride with sodium ethoxide in methanol. All of the complexes were characterized by elemental analysis, FT-IR, NMR (1H, 13C, and 119Sn) spectroscopy, TGA, and X-ray crystallography. Crystal structures show that all of the complexes are generated by the bidentate oxygen atoms and the five-coordinated tin centers with trigonal bipyramid geometry. The structural analyses reveal that complex 1 has a centrosymmetric tetranuclear triorganotin selenite with 16-membered macrocycle, which is formed by trimethyltin and ligand alternate linking. A series of C–H···O and π–π stacking interactions in complex 1 play an important function in the supramolecular aggregation. Complex 3 has two 1D spring-like chiral helical chains and crystallizes in the monoclinic space group P21, which is chiral. Complex 2 and 4 are both 1D infinite neutral chain polymers and complex 2 forms a 2D supramolecular framework through intermolecular C–H···O interactions.

Organotin(IV) compounds containing N,C,O-chelating ligand

A set of organotin(IV) compounds containing unsymmetrical N,C,O-chelating ligands {C6H3(CH2OMe)-2-(CH2NMe2)-6}− (hereafter denoted as L1) and {C6H3(CH2OtBu)-2-(CH2NMe2)-6}− (hereafter denoted as L2) was prepared. While triorganotin(IV) chlorides L1–2Ph2SnCl (1 for L1, 2 for L2) are stable, diorganotin(IV) chloride L1PhSnCl2 (3) and monoorganotin(IV) bromide L1SnBr3 (5) reacts with water under elimination of HX (X=Cl, Br). The reaction of another molecule 3 or 5 with HX (X=Cl, Br) provided “stannatrane type” compounds [{C6H3(CH2OMe)-2-(CH2N+HMe2)-6}(Ph)SnCl3] (4) and [{C6H3(CH2OMe)-2-(CH2N+HMe2)-6}SnBr4] (6), respectively. Compounds 1–6 were characterized by multinuclear NMR spectroscopy and molecular structures of 1, 3, 4 and 6 were determined by X-ray diffraction analysis.