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1.
Triorganotin(IV) complexes of the 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylic acid (HL), Me3SnL(H2O), (1), [n-Bu3SnL]2(H2O), (2), Ph3SnL(MeOH), (3), were synthesized by reacting the amino acid with organotin(IV) hydroxides or oxides in refluxing methanol. The complexes have been characterized by elemental analysis, 1H, 13C and 119Sn NMR, IR, Raman and 119Sn Mössbauer spectroscopic techniques. Single crystal X-ray diffraction data were obtained for compounds (2) and (3). Ph3SnL(MeOH) presents a trigonal bipyramidal structure with the organic groups on the equatorial plane and the axial positions occupied by a ligand molecule, coordinated to tin through the carboxylate, and a solvent molecule, MeOH. A similar structure is proposed for Me3SnL(H2O) on the basis of analytical and spectroscopic data. The tributyltin(IV) derivative, [n-Bu3SnL]2(H2O), is characterized by two different tin sites with similar tbp geometry featured by butyl groups on the equatorial plane. Sn(1) and Sn(2) atoms are axially bridged by a ligand molecule binding through the N(4) and the carboxylate group; the two coordination spheres are saturated by another ligand molecule, binding the metal through the carboxylate group, and a water molecule, respectively. Antimicrobial tests on compounds 1 and 2 showed in vitro activity against Gram-positive bacteria.  相似文献   

2.
Some five- and six-coordinated di- and tri-n-butyl tin(IV) complexes of the type Bu2SnL, Bu2SnL2 and Bu3SnL (where L is the anion of a monofunctional bidentate or bifunctional tridentate Schiff base) have been synthesized and characterised on the basis of microanalyses, molecular weight determinations, IR, NMR (1H, 13C, 119Sn) and 119Sn Mössbauer spectroscopy. These complexes are highly active towards bacteria.  相似文献   

3.
Javed  F.  Ali  S.  Shahzadi  S.  Tahir  M. N.  Tabassum  S.  Khalid  N. 《Russian Journal of General Chemistry》2016,86(12):2768-2776

Organotin(IV) O-butyl carbonodithioates [Me2SnL2], [Bu2SnL2], [Ph2SnL2], [Bu3SnL], and [Ph3SnL], where L = C4H9OCS 2 , have been successfully synthesized and characterized by FT-IR, 1H and 13C NMR, and single crystal X-ray analysis. The ligand coordinates to the tin atom via the carbonodithioate group. According to the X-ray diffraction data, the tin atom in [Me2SnL2] has distorted tetrahedral geometry. The synthesized compounds were screened in vitro for antibacterial, antifungal, antileishmanial, cytotoxic, and protein kinase inhibitory activities. The complexes [Bu3SnL] and [Ph3SnL] exhibited the highest anti-leishmanial activity that exceeded the activity of the reference drug amphotericin B, probably by blocking the function of parasitic mitochondria due to which it restricts further growth of the organisms. The ligand and the complexes have been shown to bind to DNA via intercalative interactions resulting in hypochromic effect with a minor red shift as confirmed by UV-Vis spectroscopic studies.

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4.
Some five- and six-coordinated di and tri-n-butyl tin(IV) semi- and thio-semi carbazates have been synthesized. The characterization of these complexes, by IR, NMR (1H, 13C, 119Sn), 119Sn), 119Sn Mössbauer and Mass spectroscopies along with X-ray diffraction, reveals that complexes of biionic ligands of the type Bu2Sn L″ are five-coordinated having trigonal bipyramidal geometry. However, complexes of monoionic ligands of the type Bu2SnL′2 are six-coordinated in a distorted cis-octahedral geometry and Bu3SnL′ are five-coordinated with a trigonal bipyramidal structure. X-ray structural studies on the compound Bu2Sn(O.C6H4.CH:N.N.CS.NH2), show that it crystallizes in a monoclinic lattice with a = 16.90 Å, b = 9.71 Å, c = 8.60 Å, and β = 103°45′.  相似文献   

5.
Complexes [Me2SnL2 ( I ), Me3SnL ( II ), Et2SnL2 ( III ), n‐Bu2SnL2 ( IV ), n‐Bu3SnL ( V ), n‐Oct2SnL2 ( VI )], where L is (E)‐3‐furanyl‐2‐phenyl‐2‐propenoate, have been synthesized and structurally characterized by vibrational and NMR (1H, 13C and 119Sn) spectroscopic techniques in combination with mass spectrometric and elemental analyses. The IR data indicate that in both the di‐ and triorganotin(IV) carboxylates the ligand moiety COO acts as a bidentate group in the solid state. The 119Sn NMR spectroscopic data, 1J[119Sn,13C] and 2J[119Sn, 1H], coupling constants show a four‐coordinated environment around the tin atom in triorganotin(IV) and five‐coordinated in diorganotin(IV) carboxylates in noncoordinating solvents. The complexes have been screened against bacteria, fungi, and brine‐shrimp larvae to assess their biological activity. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:612–620, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20488  相似文献   

6.
Four new organotin (IV) complexes with general formula R3SnL/R2SnL2, where R = CH3, n-C4H9, C6H5 and L = Levofloxacin, were synthesized and characterized by elemental analyses, FT-IR and NMR (1H and 13C) spectroscopy. Spectroscopic data suggested a six-coordinated geometry for diorganotin(IV) derivatives and a five-coordinated geometry for triorganotin(IV) derivatives. The value of Me–Sn–Me bond angle for di- and trimethyltin complexes using the Lockhart equation, were 150° and 116°, respectively, that corresponded to six and five-coordinate geometry, accordingly. The ligand and its complexes were screened for their antibacterial, antifungal, cytotoxic, and free radical scavenging (DPPH) antioxidant activities. The biological data indicated those as potentially bioactive in each field of the study. Accumulated data of DNA interaction with the synthesized complexes based on UV-Vis, cyclic voltammetry and viscometry suggested an intercalative mode of the interaction.  相似文献   

7.
8.
Reaction of tin dichloride and tin tetrachloride with cyclohexylamine-N-thiohydrazide (ChaThz) [L1] and 1,3-propanediamine-N-thiohydrazide (PdaThz) [L2] results in [Sn(ChaThz)2] (1), Sn(ChaThz)2Cl2] (2), [Sn(PdaThz)2] (3), and [Sn(PdaThz)2Cl2] (4), in which the thiohydrazide coordinates to tin through imine nitrogen and thioamide sulfur. The ratio metal?:?ligand was 1?:?2 for all complexes. The tin(IV) thiohydrazide complexes were characterized by elemental analysis, IR, UV-Vis, 1H-NMR, 119Sn NMR, and mass spectral studies. Using the disc diffusion method, the ligands and metal complexes were screened for in vitro antibacterial activities against four pathogenic bacteria, Escherichia coli, Staphylococcus aureus, P. aeruginosa, and Bacillus cereus and for antifungal activities against Aspergillus flavus, A. carbonarius, A. niger, and A. fumigatus. While the tin(IV) complexes exhibited moderate antifungal activities, their parent ligands showed much higher and long-lasting broad spectrum of bioactivity against fungal growth. This was particularly the case for L1 whose fungal inhibitory activity by the end of the experimental period was comparable and, for the most part, more pronounced than that of AmB. This higher activity of L1 was maintained specifically against S. Aureus but in general, bacteria were more susceptible to complexes than ligands.  相似文献   

9.
New organotin(IV) compounds containing the carboxylate ligand 2,3-methylenedioxybenzoic acid (HL) have been synthesized with the general formula R2SnL2 (R = Me, Et, n-Bu, Ph and n-Oct) and R3SnL (R = n-Bu). All compounds have been studied in the solution state by multinuclear NMR (1H, 13C and 119Sn) by using the non-coordinating solvent and also in solid sate by FTIR, mass spectrometry and X-ray crystallography. Spectroscopic data have shown that methylenedioxy moiety does not coordinate with tin atom and the coordination site is actually -COO group, as is proved by X-ray structure determination. The solid state structure of compound (2) has been determined by X-ray crystallography which shows that the complex (2) has distorted octahedral geometry. These complexes have been evaluated in vitro against crown gall tumor and antibacterial activity. Interesting results were noticed during the bio-activity screenings, which proved their in vitro biological potential and possible use as drugs.  相似文献   

10.
The diorganotin(IV) complexes of methyl 2‐{4‐hydroxy‐3‐[(2‐hydroxy‐phenylimino)‐methyl]‐phenylazo}‐benzoate (H2L) were obtained by the reaction of ortho‐aminophenol, R2SnO (R = Me, nBu, or Ph) and methyl 2‐[(E)‐(3‐formyl‐4‐hydroxy)diazenyl]benzoate (H2PL2) in ethanol, which led to diorganotin(IV) compounds of composition [Me2SnL]2 ( 1 ), nBu2SnL ( 2 ), and Ph2SnL ( 3 ) in good yield. The 1H, 13C, and 119Sn NMR, IR, the mass spectrometry along with elemental analyses allowed establishing the structure of ligand (H2L) and compounds 1–3 . In all the three cases, 119Sn chemical shifts are indicators of five‐coordinated Sn atoms in a solution state. The crystal structures of ligand H2L and complexes 1 and 2 were determined by a single crystal X‐ray diffraction study. In the solid state, the ligand H2L exists as a keto‐enamine tautomeric form. The molecular structure of complex 1 in the solid state shows a distorted octahedral geometry around a tin atom due to additional coordination with an oxygen atom from a neighboring molecule leading to a four‐membered ring with Sn‐O···Sn‐O intermolecular coordination, leading to a dimeric species. On the other hand, complex 2 is a monomer with trigonal bipyramidal geometry surrounding the tin atom. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:457–465, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.21037  相似文献   

11.
Abstract

Six organotin(IV) complexes of type Me2SnL2, Bu2SnL2, and Ph3SnL [where L = indole-3-butyric acid (1, 2 and 3) or indole-3-propionic acid (4, 5 and 6)] have been synthesized by the reactions of the corresponding diorganotin(IV) oxide and triphenyltin(IV) hydroxide with respective indole-3-butyric acid (IBH) or indole-3-propionic acid (IPH) in the desired molar ratios of 1:2/1:1. All of the compounds have been characterized by elemental analysis, IR, 1H NMR, 13C NMR, and 119Sn NMR spectroscopy. Thermal studies of all synthesized complexes have been carried out using thermogravimetry (TG) technique under a nitrogen atmosphere. The thermal decompositions for compounds Me2SnL2 and Bu2SnL2 occurred in two steps, whereas in compounds Ph3SnL, it exhibited as three steps decomposition and resulted into the formation of pure SnO2. The complexes were also screened against three gram-positive (Staphylococcus aureus, Staphylococcus epidermidis, and Micrococcus luteus) and three gram-negative (Escherichia coli, Pseudomonas aeruginosa, and Enterobacter aerogenes) bacteria using minimum inhibition concentration (MIC) method, and all of these complexes showed significant antibacterial activity.

[Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text, tables, and figures.]  相似文献   

12.
The one pot reactions carried among ortho-aminophenol, R2SnO (R = Me or Ph) and acetyl acetone, 2-hydroxyacetophenone and 2-hydroxy-3-methylacetophenone led to six new diorganotin(IV) compounds Me2SnL1 (1), Ph2SnL1 (2), Me2SnL2 (3) Ph2SnL2 (4), Me2SnL3 (5) and Ph2SnL3 (6) (H2L1 = 2-(3-hydroxy-1-methyl-but-2-enylideneamino)-phenol, H2L2 and H2L3 = 2-[1-(2-hydroxyaryl)alkylideneamino]-phenol) in good yields. Combination of IR, 1H, 13C and 119Sn NMR and X-ray diffraction techniques along with elemental analyses evidenced the formation of penta-coordinated monomeric species. The crystal structures of ligand H2L1 and complexes 1, 3 and 4 were determined by single crystal X-ray diffraction study. In the solid state, the ligand H2L1 exists as keto-enamine tautomeric form. There are N-H…O intra-molecular hydrogen bonds between amine and carbonyl groups. Diorganotin(IV) complexes 1, 3 and 4 are monomers with TBP (trigonal bipyramidal) geometry surrounding the tin atom. The O, N, O- tridentate ligand places its two oxygen donating atoms in the axial positions, and the nitrogen atom occupies one equatorial position. The two R groups attached to tin occupy the other two equatorial positions. The solution structures were predicted by 119Sn NMR spectroscopy.  相似文献   

13.
Several new complexes of organotin(IV) moieties with MCln[meso-tetra(4-sulfonatophenyl)porphine], (R2Sn)2MCln[meso-tetra(4-sulfonatophenyl)-porphinate]s and (R3Sn)4MCln [meso-tetra(4-sulfonatophenyl)porphinate]s, [M = Fe(III), Mn(III): n = 1, R = Me, n-Bu; Ph; M = Sn(IV): n = 2, R = Me, n-Bu] have been synthesized and their solid state configuration investigated by infrared (IR) and Mössbauer spectroscopy, and by 1H and 13C NMR in D2O.The electron density on the metal ion coordinated inside the porphyrin ring is not influenced by the organotin(IV) moieties bonded to the oxygen atoms of the side chain sulfonatophenyl groups, as it has been inferred on the basis of Mössbauer spectroscopy and, in particular, from the invariance of the isomer shift of the Fe(III) and Sn(IV) atoms coordinated into the porphyrin square plane of the newly synthesized complexes, with respect to the same atoms in the free ligand.As far as the coordination polyhedra around the peripheral tin atoms are concerned, infrared spectra and experimental Mössbauer data would suggest octahedral and trigonal bipyramidal environments around tin, in polymeric configurations obtained, respectively, in the diorganotin derivatives through chelating or bridging sulfonate groups coordinating in the square plane, and in triorganotin(IV) complexes through bridging sulfonate oxygen atoms in axial positions.The structures of the (Me3Sn)4Sn(IV)Cl2[meso-tetra(4-sulfonatophenyl)porphinate] and of the two model systems, Me3Sn(PS)(HPS) and Me2Sn(PS)2 [HPS = phenylsulfonic acid], have been studied by a two layer ONIOM method, using the hybrid DFT B3LYP functional for the higher layer, including the significant tin environment. This approach allowed us to support the structural hypotheses inferred by the IR and Mössbauer spectroscopy analysis and to obtain detailed geometrical information of the tin environment in the compounds investigated.1H and 13C NMR data suggested retention of the geometry around the tin(IV) atom in D2O solution.  相似文献   

14.
A series of some new mixed ligand complexes have been synthesized with an objective for evaluation as antimicrobials. Reactions of diorganotin(IV) dichloride with dibenzoyl methane and O‐alkyl trithiophosphates in a 1:1:1 molar ratio in refluxing benzene yield products of the type [PhCOCHCOPh]R2Sn‐[SSH(S)POR'] [where R = Me, Bu, Ph; R' = Me, Et, Pri, Bui, Ph]. The newly synthesized complexes are light yellow colored crystalline solids, non‐volatile, soluble in common organic solvents, monomeric in nature and highly sensitive towards atmospheric moisture. These complexes are characterized by elemental analysis, IR and multinuclear NMR (1H, 31P and 119Sn) spectral studies. Spectral studies of these complexes indicate that dibenzoyl methane and O‐alkyl trithiophosphate moieties are bidentate and the central tin atom is hexacoordinated in nature. A few of these compounds were tested for their antibacterial activity using standard drugs.  相似文献   

15.
The preparation and structures of 2, 2′‐dihydroxyazobenzenato‐dibutyl‐tin [Bu2SnL] and 2, 2′‐dihydroxyazobenzenato‐dimethyl‐tin [Me2SnL] are described. The complexes were characterized by IR, NMR (1H, 13C, 119Sn) and UV/VIS spectra. The crystal structures were determined by X‐ray diffraction on single crystals. [Bu2SnL]: monoclinic, space group P21/c, cell constants at 208 K: a = 860.73(5), b = 973, 51(18), c = 2340.0(3) pm, β = 93.615(11)°; R1 = 0.0546. [Me2SnL]: orthorhombic, space group Pbcn, cell constants at 208 K: a = 1914.6(4), b = 1041.3(3), c = 1323.27(14) pm; R1 = 0.0529.  相似文献   

16.
A series of six organotin(IV) carboxylates [Me2SnL2] (1), [n-Bu2SnL2] (2), [n-Oct2SnL2] (3), [Me3SnL] (4), n-Bu3SnL (5) and [Ph3SnL] (6), where L = 3-(4-cyanophenyl) acrylic acid have been synthesized and characterized by elemental analysis, FT-IR and NMR (1H, 13C). The complex (4) was also analyzed by single crystal X-ray analysis which showed distorted trigonal bipyramidal geometry with polymeric bridging behavior. The complexes 16 were screened for antimicrobial activities and cytotoxicity. The results showed significant activity with few exceptions. The catalytic activity of complexes was assessed in transesterification reaction of Brassica campestris oil (triglycerides) to produce biodiesel (fatty acid methyl esters). The results showed that triorganotin(IV) complexes exhibited good catalytic activity than their di-analogues.  相似文献   

17.
《Polyhedron》1999,18(20):2687-2696
Diorganotin(IV) complexes of the general formula R2SnL (R=Ph, n-Bu and Me) have been prepared from diorganotin(IV) dichlorides (R2SnCl2) and tetradentate Schiff bases (H2L) containing N2O2 donor atoms in the presence of triethylamine in benzene. The Schiff bases, H2L, were derived from salicylaldehyde, 3-methoxysalicylaldehyde (o-vanillin), 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and diamines such as o-phenylenediamine and 1,3-propylenediamine. The complexes were characterized by IR, NMR (1H, 13C, 119Sn) and elemental analysis. The structure of the complex, n-Bu2Sn(Vanophen), was determined using single crystal X-ray diffraction. The tin atom has a distorted octahedral coordination, with the Vanophen ligand occupying the four equatorial positions and the n-butyl groups in the trans axial positions. Six-coordinated distorted octahedral structures have been proposed for all diorganotin(IV) complexes studied here, as they possess similar spectroscopic data.  相似文献   

18.
Eight tri‐ and diorganotin(IV) carboxylates with general formulae R3SnL and R2SnL2 (where R = CH3, n‐C4H9, C6H5, C7H7, and L = 2′,4′‐difluoro‐4‐hydroxy‐[1,1′]‐biphenyl‐3‐carboxylic acid) were synthesized and characterized by UV–vis, IR, conductance, multinuclear (1H, 13C, and 119Sn) NMR spectroscopy, and mass spectrometry. The crystal structure of [(CH3)3Sn(C13H7O3F2)] indicates that the tin atom in the asymmetric unit exists in a trigonal bipyramidal geometry having a space group Pbca with an orthorhombic crystal system. These complexes were also screened for their antibacterial and antifungal activities. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:638–649, 2002; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10057  相似文献   

19.
Triorganotin(IV) complexes of the type Me3Sn[OC(R1):CH(CH3)C:NR2OH] and Ph3Sn[OC(R′):CH(CH3)C:NR″OH] (R′ = ─CH3, ─C6H5; R″ = ─(CH2)2─, ─(CH2)3─) have been synthesized by the reactions of trimethyl/phenyltin(IV) chloride with the sodium salt of corresponding Schiff base ligands in unimolar ratio in refluxing tetrahydrofuran. All these compounds have been characterized using elemental analyses and their probable structures have been proposed on the basis of infrared, 1H NMR, 13C NMR, 119Sn NMR and mass spectroscopic studies. In the trimethyltin(IV) derivatives the central tin atom is tetracoordinated, whereas in the analogous triphenyltin(IV)derivatives the central tin atom is pentacoordinated. All these ligands, metal precursors and corresponding triorganotin(IV) complexes have been screened for antimicrobial activities. A comparison of activities of the ligands and their corresponding triorganotin(IV) derivatives has been made. Attempts have also been made to relate the activity to the structure of these compounds.  相似文献   

20.
Three new diorganotin(IV) complexes, [Me2Sn(BDET] (2), [Bu2Sn(BDET)] (3), and [Ph2Sn(BDET)] (4), were synthesized by reacting R2SnCl2 (R = Me, Bu, and Ph) with 5-bromo-2-hydroxybenzaldehyde-N(4)-ethylthiosemicarbazone [H2BDET, (1)] in the presence of KOH in absolute methanol. The newly synthesized complexes were characterized by elemental analysis, molar conductivity, UV–vis, FT-IR, 1H, 13C, and 119Sn NMR spectroscopies. The molecular structure of 4 was confirmed by X-ray crystallography. X-ray crystallography revealed that the doubly deprotonated O,N,S-tridentate thiosemicarbazone coordinates to tin(IV), resulting in a distorted trigonal bipyramidal geometry. Their 1H, 13C, and 119Sn NMR spectra support a five-coordinate tin(IV) in solution for all complexes, in accord with the solid-state X-ray structure determined for 4. Compounds 14 were evaluated for their antibacterial activities against Staphylococcus aureus, Enterobacter aerogenes, Escherichia coli, and Salmonella typhi. The results exhibited that 24 were active with comparable potency compared to the standard drug. Antibacterial studies also indicated that the complexes have potential for biological evaluation.  相似文献   

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