Antimony(III) and bismuth(III) complexes containing O- and N-chelating ligands: synthesis, FT-IR, 1H and 13C NMR spectroscopic and mass spectrometric studies
-
Ajeet Kumar Kushwaha
Abstract
Reaction of SbCl3 with sodium salt of vanillinidene-2-methylaminobenzene (vmabH) and salicylidene-3-nitroaminobenzene (snabH) in 1:1 and 1:2 molar ratios afforded complexes of the type [Sb(η2-sb)nCl3−n ](1–4) [where sb=vanillinidene-2-methyl-1-aminobenzene (vmabH) (1, 2) and salicylidene-3-nitroaminobenzene (snabH) (3, 4)]. Bismuth complexes of type [Bi(PBT)nCl3−n ] (5, 6) have been synthesized similarly by the reaction of BiCl3 with sodium salt of 2-(o-hydroxyphenyl)-benzothiazole (HPBT) in different molar ratios (where n=1−2). These newly synthesized complexes of antimony and bismuth have been characterized by elemental (C, H, N, S, Sb, and Bi) analysis and spectroscopic IR, 1H NMR, and 13C NMR techniques. The molecular composition of three selective complexes has been confirmed by mass spectrometric studies.
Introduction
Antimony and bismuth complexes derived from Schiff bases are given considerable importance due to their significant biological properties which lead to therapeutic effect (Tiekink, 2002; Ge and Sun, 2007). Antimony complexes have shown significant potential against tumor cell (Hadjikakou et al., 2015) and are used as antileishmanial (Khan et al., 2011), anthelminthic (Newlove et al., 2011), antitrypanosomal (Parrilha et al., 2012), antimicrobial (Kasuga et al., 2006), and anticancer (Ozturk et al., 2012) agents. Furthermore, antimony complexes have shown prominent application in catalysis (Ning et al., 2016). Bismuth(III) complexes are well acknowledged for their role in organic synthesis (Bothwell et al., 2011), nano material synthesis (Stavila et al., 2009), medicine (Briand and Burford, 1999), and biocoordination (Yang and Sun, 2007). Recently Bi(III) Schiff base complexes demonstrated strong inhibitory action against microbes (Li et al., 2015) and as antibiotics against Helicobacter pylori (Andrews et al., 2014; Pathak et al., 2015). Taking above facts in view, our interest in main group metal complexes (Dubey et al. 2011b, 2013, 2014) prompts us to synthesize antimony and bismuth complexes with biologically potent ligands such as 2-(o-hydroxyphenyl)-benzothiazole (HPBT) (Singh et al. 2014), which also is known for its electroluminescent properties (Yu et al., 2003) and Schiff bases (Dubey et al. 2011a, 2012, 2014) derived by condensation of o-vanillin, salicylaldehyde with o-toluidine, m-nitroaniline, respectively.
Results and discussion
The antimony(III) complexes 1–4 have been prepared by the reaction of antimony trichloride with sodium salt of vanillinidene-2-methylaminobenzene (vmabH) and salicylidene-3-nitroaminobenzene (snabH) in 1:1 and 1:2 ratios as shown in Scheme 1. Bismuth(III) complexes have been synthesized by the reaction of bismuth trichloride with sodium salt of 2-(o-hydroxyphenyl)-benzothiazole (HPBT) in different molar ratios as shown in Scheme 2. Antimony complexes are dark yellow to brown colored solids, whereas bismuth complexes are creamy white solid. These complexes are insoluble in organic solvents and soluble in polar solvents. Some physical properties of these complexes are summarized in Table 1.
General method for the preparation of Schiff bases and antimony(III) complexes.
General method for the preparation of bismuth(III) complexes.
Synthetic and analytical details of antimony(III) and bismuth(III) complexes 1–6.
| Complex empirical formula | Mol. wt. | Physical state | MP (°C) | Yield % | % Elemental analysis found (calcd) | ||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| C | H | N | S | Cl | Sb | Bi | |||||
| vmabH I C15H15NO2 | 241.29 | Orange solid | 95 | 78 | 74.25 (74.67) | 6.40 (6.27) | 5.69 (5.81) | – | – | – | – |
| [Sb(η2-vmab)Cl2] 1 C15H14Cl2NO2Sb | 432.94 | Dark yellow solid | 140 | 64 | 41.13 (41.61) | 3.11 (3.26) | 3.85 (3.24) | – | 16.85 (16.38) | 27.95 (28.12) | – |
| [Sb(η2-vmab)2Cl] 2 C30H28ClN2O4Sb | 637.77 | Dark yellow solid | 132 | 60 | 56.48 (56.50) | 4.63 (4.43) | 4.20 (4.39) | – | 5.55 (5.56) | 18.87 (19.09) | – |
| snabH II C13H10N2O3 | 242.23 | Yellow solid | 105 | 82 | 64.12 (64.46) | 4.29 (4.16) | 11.23 (11.56) | – | – | – | – |
| [Sb(η2-snab)Cl2] 3 C13H9Cl2N2O3Sb | 433.89 | Brown solid | 125 | 69 | 35.85 (35.99) | 2.12 (2.09) | 6.80 (6.46) | – | 16.20 (16.34) | 28.50 (28.06) | – |
| [Sb(η2-snab)2Cl] 4 C26H18ClN4O6Sb | 639.66 | Brown solid | 148 | 62 | 48.75 (48.82) | 2.55 (2.84) | 8.75 (8.76) | – | 5.62 (5.54) | 19.10 (19.04) | – |
| HPBT III C13H9NOS | 227.28 | White solid | 130 | – | 68.65 (68.70) | 3.75 (3.99) | 6.25 (6.16) | 14.00 (14.11) | – | – | – |
| [Bi(PBT)Cl2] 5 C13H8BiCl2NOS | 506.16 | Creamy white solid | 165 | 61 | 30.75 (30.82) | 1.49 (1.59) | 2.71 (2.77) | 6.25 (6.33) | 14.25 (14.01) | – | 40.93 (41.29) |
| [Bi(PBT)2Cl] 6 C26H16BiClN2O2S2 | 696.98 | Creamy white solid | 172 | 59 | 44.23 (44.80) | 2.20 (2.31) | 4.18 (4.02) | 9.45 (9.20) | 5.19 (5.09) | – | 29.64 (29.98) |
IR spectroscopy
Salient absorption bands were observed in IR spectra for complexes 1–6 and free ligands, which are summarized in Table 2. The characteristic feature of the IR spectra of the complexes is disappearance of phenolic stretching vibration v(O-H) observed in free ligands in the region 3564–3343 cm−1 due to deprotonation of phenolic hydrogen (Viswanathamurthi et al., 2000), which was further supported by shift of v(C-O) band ~10–20 cm−1 higher frequency region in complexes compared to free ligands in the region 1272–1295 cm−1 (Dubey and Singh, 2013) and appearance of new bands in the regions 573–580 and 546–570 cm−1 for bismuth and antimony complexes, respectively (Durgashanker and Singh, 2007). The involvement of azomethine nitrogen in bonding in complexes was supported by shifting of νC=N towards lower frequency 1615–1598 cm−1 region compared to free ligands 1634–1616 cm−1 region (Vajpayee and Singh, 2007) and appearance of new bands in the region 580–540 cm−1 due to M←N stretching vibration (Dawara and Singh, 2011).
Characteristic IR frequencies (cm−1) of new antimony(III) and bismuth(III) complexes 1–6.
| Complex | v(OH) | v(C=N) | v(C-O) Phenolic | vM←N | v(M-O) |
|---|---|---|---|---|---|
| vmabH | 3564 | 1617 | 1272 | – | – |
| [Sb(η2-vmab)Cl2] 1 | – | 1608 | 1282 | 438 | 570 |
| [Sb(η2-vmab)2Cl] 2 | – | 1611 | 1284 | 438 | 580 |
| snabH | 3343 | 1614 | 1277 | – | – |
| [Sb(η2-snab)Cl2] 3 | – | 1609 | 1283 | 440 | 578 |
| [Sb(η2-snab)2Cl] 4 | – | 1607 | 1286 | 439 | 546 |
| HPBT | 3405 | 1640 | 1295 | – | – |
| [Bi(PBT)Cl2] 5 | – | 1622 | 1315 | 455 | 573 |
| [Bi(PBT)2Cl] 6 | – | 1620 | 1314 | 455 | 580 |
1H NMR spectroscopy
The 1H NMR spectra recorded in DMSO-d6 using tetramethylsilane as internal reference and 1H NMR data of free ligands and their complexes 1–6 are collected in Table 3. A comparison of 1H NMR spectra of ligand with metal complexes can lead to the following conclusions: (i) 1H NMR spectra of complexes 1–6 exhibit no signal due to phenolic hydrogen (OH) observed at 13.20–12.76 ppm in the ligands, indicating metallation of phenolic group (OH) (Dubey et al., 2014); (ii) shifting of azomethine hydrogen signal to a higher region 9.93–8.32 ppm compared to parent Schiff bases (9.23–8.23 ppm) supporting coordination of azomethine nitrogen to metal atom (Solanki et al., 2009).
1H NMR data (ppm) for new complexes 1–6.
| Complex | HC=N | Ar-H | Ar-OH | -OCH3 | -CH3 |
|---|---|---|---|---|---|
| vmabH | 8.50 (s, 1H) | 6.8–7.8 (m, 7H) | 13.20 (s, 1H) | 3.81 (s, 3H) | 2.38 (s, 3H) |
| [Sb(η2-vmab)Cl2] 1 | 9.66 (s, 1H) | 7.8–8.0 (m, 7H) | – | 3.89 (s, 3H) | 2.40 (s, 3H) |
| [Sb(η2-vmab)2Cl] 2 | 9.79 (s, 2H) | 7.0–8.0 (m, 14H) | – | 3.94 (s, 6H) | 2.40 (s, 6H) |
| snabH | 8.46 (s, 1H) | 6.6–7.9 (m, 8H) | 12.67 (s, 1H) | – | – |
| [Sb(η2-snab)Cl2] 3 | 9.76 (s, 1H) | 6.9–8.0 (m, 8H) | – | – | – |
| [Sb(η2-snab)2Cl] 4 | 9.57 (s, 2H) | 6.9–7.9 (m, 16H) | – | – | – |
| HPBT | 8.23 (s, 1H) | 6.8–7.8 (m, 8H) | 11.74 (s, 1H) | – | – |
| [Bi(PBT)Cl2] 5 | 9.58 (s, 1H) | 7.0–8.3 (m, 8H) | – | – | – |
| [Bi(PBT)2Cl] 6 | 9.65 (s, 2H) | 7.0–8.3 (m, 16H) | – | – | – |
13C NMR spectroscopy
The 13C NMR data of free ligands and their complexes 1–6 are summarized in Table 4. In the 13C NMR spectra of the Schiff bases, signals in the region 149.71–156.53 ppm due to azomethine carbon were shifted towards higher value in the region 152.16–159.19 ppm in the complexes, indicating the involvement of azomethine nitrogen in bonding with antimony and bismuth atom (Dubey et al., 2014). Signal due to phenolic carbon in the region 144.45–156.53 ppm shifted toward the higher value in the region 157.19–165.81 ppm, indicating the involvement of phenolic oxygen in the bonding (Dubey et al., 2011b).
13C NMR data (ppm) for new complexes of antimony(III) and bismuth(III) complexes.
| Complex | C-O phenolic | HC=N | Ar-C | -OCH3 | Ar-CH3 |
|---|---|---|---|---|---|
| vambH | 145.8 (s, 1C) | 151.6 (s, 1C) | 132.5–122.7 (s, 11C) | 54.1 (s, 1C) | 18.1 (s, 1C) |
| [Sb(η2-vmab)Cl2] 1 | 162.2 (s, 1C) | 159.1 (s, 1C) | 145.6–121.3 (s, 11C) | 53.17 (s, 1C) | 17.7 (s, 1C) |
| [Sb(η2-vmab)2Cl] 2 | 159.1 (s, 2C) | 155.5 (s, 2C) | 147.7–121.8 (s, 22C) | 54.07 (s, 2C) | 17.5 (s, 2C) |
| snabH | 144.4 (s, 1C) | 149.7 (s, 1C) | 147.4–123.2 (s, 11C) | – | – |
| [Sb(η2-snab)Cl2] 3 | 161.1 (s, 1C) | 152.1 (s, 1C) | 143.2–121.9 (s, 11C) | – | – |
| [Sb(η2-snab)2Cl] 4 | 157.1 (s, 2C) | 157.3 (s, 2C) | 139.4–120.6 (s, 22C) | – | – |
| HPBT | 158.5 (s, 1C) | 152.5 (s, 1C) | 140.3–119.2 (s, 11C) | – | – |
| [Bi(PBT)Cl2] 5 | 163.4 (s, 1C) | 154.5 (s, 1C) | 135.5–119.5 (s, 11C) | – | – |
| [Bi(PBT)2Cl] 6 | 165.8 (s, 2C) | 156.4 (s, 2C) | 133.8–117.0 (s, 22C) | – | – |
Mass spectrometry
The TOF-MS ES+ spectra of the complexes 1, 5, and 6 were recorded. In the spectra of complexes 1, 5, and 6 molecular ion peak was observed at m/z 432.45 [(C15H14Cl2NO2Sb); calculated mass=430.94], 507.39 [(C13H8BiCl2NOS); calculated mass=504.95] and 697.19 [(C26H16BiClN2O2S2); calculated mass=696.01], respectively, which correspond to the monomeric molecular composition of the complexes.
Conclusion
Synthesis of antimony(III) and bismuth(III) complexes have been achieved by the reactions of SbCl3 and BiCl3 with appropriate sodium salt of ligands in 1:1 and 1:2 molar ratios, respectively. Spectroscopic studies confirm the O- and N-atom involvment in the bonding and molecular composition of complexes was proved by the mass spectrometric studies.
Experimental
Materials
SbCl3 (Merck, Germany), BiCl3, (o-hydroxyphenyl) benzothiazole (Sigma Aldrich, Bangalore, India), o-vanillin (Alfa-aesar), o-toluidine (LOBA, Mumbai, India), m-nitroaniline, and salicylaldehyde (CDH, New Delhi, India) were used without further purification. All solvents used were of reagent grade and purified by standard procedures (Armarego and Perrin, 1997). Chlorine was estimated by Volhard’s method (Vogel, 2008) while antimony and bismuth were estimated complexometrically and iodometrically, respectively (Vogel, 2008). The Schiff bases were synthesized according to the literature method (Dubey et al., 2005).
Physical measurement
Elemental analyses for C, H, N, and S were carried out with Carlo Erba 1108 element analyzer. Melting points were measured in open tubes with a Stuart scientific apparatus and are uncorrected. Infrared spectra were recorded on a Perkin-Elmer 100 FT-IR spectrophotometer in the range 4000–400 cm−1. 1H and 13C NMR spectra were recorded on Bruker Avance II 400 NMR spectrometer in DMSO-d6 and chemical shifts were given in ppm relative to Me4Si as internal reference. ESI-MS spectra were recorded on Agilent 6520 Q-Tof LC-MS, MS/MS spectrometers in acetonitrile.
Synthesis of complexes
Similar procedure was used for the preparation of the complexes (1–6); therefore, for the sake of brevity, general preparative details are given below for complex 1. To a benzene (~20 mL) solution of SbCl3 (1.140 g, 4.99 mmol) sodium salt of Schiff base [prepared by dissolving equimolar amount of sodium metal (0.114 g, 4.99 mmol) and a Schiff base, vanillinidene-2-methylaminobenzene (1.205 g, 4.99 mmol) in MeOH (~30 mL)] was added dropwise in 1:1 molar ratio with constant stirring. The reaction mixture was allowed to reflux for ~12 h. The precipitated NaCl was removed by filtration. The solvent was removed by distillation. The solid products were dried under reduced pressure and recrystallized from the mixture of THF- n–hexane in 1:4.
Acknowledgments
The authors are thankful to UGC, New Delhi for doctoral fellowship. Authors gratefully acknowledge the SAIF Chandigarh for spectroscopic and mass analysis and CDRI Lucknow for elemental analysis.
References
Andrews, P. C.; Blair, V. L.; Ferrero, R. L.; Junk, P. C.; Kedzierski, L.; Peiris, R. M. Bismuth(III) β-thioxoketonates as antibiotics against Helicobacter pylori and as anti-leishmanial agents. Dalton Trans.2014, 43, 1279.10.1039/C3DT52544ASuche in Google Scholar PubMed
Armarego, W. L. F.; Perrin, D. D. Purification of laboratory chemicals, 4th Edition; Butterworth-Heinemann: Oxford, 1997.Suche in Google Scholar
Bothwell J. M.; Krabbez, S. W.; Mohan, R. S. Applications of bismuth(III) complexes in organic synthesis. Chem. Soc. Rev.2011, 40, 4649–4707.10.1039/c0cs00206bSuche in Google Scholar PubMed
Briand, G. G.; Burford, N. Bismuth complexes and preparations with biological or medicinal relevance. Chem. Rev.1999, 99, 2601–2657.10.1021/cr980425sSuche in Google Scholar PubMed
Dawara, L.; Singh, R. V. Microwave-assisted synthesis, characterization, antimicrobial, and pesticidal activity of bismuth and antimony complexes with coumarin-based ligands. J. Coord. Chem. 2011, 64, 931–941.10.1080/00958972.2011.557721Suche in Google Scholar
Dubey, R. K.; Mishra, A. N.; Mishra, C. M. Synthesis, reactivity and physico-chemical studies of some novel mixed ligand complexes of copper(II). Indian J. Chem.2005, 44, 1159–1164.Suche in Google Scholar
Dubey, R. K.; Dubey, U. K.; Mishra, S. K. Synthesis, spectroscopic (IR, electronic, FAB-mass and PXRD), magnetic and antimicrobial studies of new iron(III) complexes containing Schiff bases and substituted benzoxazole ligands. J. Coord. Chem.2011a, 64, 2292–2301.10.1080/00958972.2011.594886Suche in Google Scholar
Dubey, R. K.; Singh, A. P.; Dwivedi, N. Synthesis and physicochemical characterization of some hexacoordinated tin(IV) Schiff base complexes. Main Group Met. Chem.2011b, 34, 77–83.10.1515/MGMC.2011.014Suche in Google Scholar
Dubey, R. K.; Baranwal, P.; Jha, A. K. Zinc(II) and mercury(II) complexes with Schiff bases: syntheses, spectral, and structural characterization. J. Coord. Chem.2012, 65, 2645–2656.10.1080/00958972.2012.699634Suche in Google Scholar
Dubey, R. K.; Singh, A. P. Dimeric and monomeric six-coordinate tin(IV) complexes: synthesis and spectral (IR, NMR (1H, 13C, 119Sn), TOF-MS, and ESI-MS) studies. J. Coord. Chem.2013, 66, 2201–2207.10.1080/00958972.2013.800975Suche in Google Scholar
Dubey, R. K.; Singh, A. P.; Patil, S. A. Synthesis, spectroscopic characterization and DNA cleavage studies of dibutyltin(IV) complexes of bidentate Schiff bases. Inorg. Chim. Acta2014, 410, 39–45.10.1016/j.ica.2013.10.012Suche in Google Scholar
Durgashanker; Singh Y. Studies on homo- and hetero- dinuclear derivatives of antimony(III) containing Schiff base ligands. Phosphorus, Sulfur, Silicon Relat. Elem.2007, 182, 1805–1817.10.1080/10426500701323358Suche in Google Scholar
Ge, R.; Sun, H. Bioinorganic chemistry of bismuth and antimony: target sites of metallodrugs. Acc. Chem. Res.2007, 40, 267–274.10.1021/ar600001bSuche in Google Scholar PubMed
Hadjikakou, S. K.; Ozturk, I. I.; Banti, C. N.; Kourkoumelis, N.; Hadjiliadis N. Recent advances on antimony(III/V) complexes with potential activity against tumor cells. J. Inorg. Biochem.2015, 153, 293–305.10.1016/j.jinorgbio.2015.06.006Suche in Google Scholar PubMed
Kasuga, N.C.; Onodera, K.; Nakano, S.; Hayashi, K.; Nomiya, K. Syntheses, crystal structures and antimicrobial activities of 6-coordinate antimony(III) complexes with tridentate 2-acetylpyridine thiosemicarbazone, bis(thiosemicarbazone) and semicarbazone ligands. J. Inorg. Biochem.2006, 100, 1176–1186.10.1016/j.jinorgbio.2006.01.037Suche in Google Scholar PubMed
Khan, M. I.; Gul, S.; Hussain, I.; Khan, M. A.; Ashfaq, M.; Rahman, I. U.; Ullah, F.; Durrani, G. F.; Baloch, I. B.; Naz, R. In vitro anti-leishmanial and anti-fungal effects of new Sb III carboxylates. Org. Med. Chem. Lett.2011, 1, 1–7.10.1186/2191-2858-1-2Suche in Google Scholar
Li, C-H; Jiang, J-H.; Li, X.; Tao, L-M.; Xiao, S. X.; Hui, H. W.; Zhang, H.; Jiang, C.; Xie, J-Q.; Peng, M. N.; et al. Synthesis, crystal structure and biological properties of a bismuth(III) Schiff-base complex. RSC Adv.2015, 5, 94267–94275.10.1039/C5RA19370BSuche in Google Scholar
Newlove, T.; Guimarães, L. H.; Morgan, D. J.; Alcântara, L.; Glesby, L.; Carvalho, E. M.; Machado, P. R. Antihelminthic therapy and antimony in cutaneous leishmaniasis: a randomized, double-blind, placebo-controlled trial in patients co-infected with helminthes and Leishmaniabraziliensis. Am. J. Trop. Med. Hyg.2011, 84, 551–555.10.4269/ajtmh.2011.10-0423Suche in Google Scholar PubMed PubMed Central
Ning, X.; Li, Y.; Yu, H.; Peng, F.; Wang, H.; Yang, Y. Promoting role of bismuth and antimony on Pt catalysts for the selective oxidation of glycerol to dihydroxyacetone. J. Catal. 2016, 335, 95–104.10.1016/j.jcat.2015.12.020Suche in Google Scholar
Ozturk, I. I.; Banti, C. N.; Manos, M. J.; Tasiopoulos, A. J.; Kourkoumelis, N.; Charalabopoulos, K.; Hadjikakou, S. K. Synthesis, characterization and biological studies of new antimony(III) halide complexes with ω-thiocaprolactam. J. Inorg. Biochem.2012, 109, 57–65.10.1016/j.jinorgbio.2012.01.014Suche in Google Scholar PubMed
Parrilha, G. L.; Dias, R. P.; Rocha, W. R.; Mendes, I. C.; Benítez, D.; Varela, J.; Cerecetto, H.; González, H.; Melo, C. M. L.; Neves, J. K. A. L.; et al. 2-Acetylpyridine and 2-benzoylpyridine-derived thiosemicarbazones and their antimony(III) complexes exhibit high anti-trypanosomal activity. Polyhedron2012, 31, 614–621.10.1016/j.poly.2011.10.018Suche in Google Scholar
Pathak, A.; Blair, V. L.; Ferrero, R. L.; Junk, P. C.; Tabora R. F.; Andrews, P. C. Synthesis and structural characterisation of bismuth(III) hydroxamates and their activity against Helicobacter pylori. Dalton Trans.2015, 44, 16903.10.1039/C5DT02259BSuche in Google Scholar
Singh, M.; Singh, S. K.; Gangwar, M.; Nath, G.; Singh, S. K. Design, synthesis and mode of action of some benzothiazole derivatives bearing an amide moiety as antibacterial agents. RSC Adv.2014, 4, 19013–19023.10.1039/C4RA02649GSuche in Google Scholar
Solanki, J. S.; Tripathi, U. N.; Bhardwaj, A.; Jena, V. K. Synthesis, spectral studies, and antimicrobial evaluation of antimony(III) tri[3(2′- hydroxyphenyl)-5-(4-substituted aryl] pyrazolinate. Phosphorus, Sulfur Silicon Relat. Elem.2009, 184, 2169–2178.10.1080/10426500802429799Suche in Google Scholar
Stavila, V.; Whitmire, K. H.; Rusakova, I. Synthesis of Bi2S3 nanostructures from bismuth(III) thiourea and thiosemicarbazide complexes. Chem. Mater.2009, 21, 5456–5465.10.1021/cm902229xSuche in Google Scholar
Tiekink, E. R. T. Antimony and bismuth complexes in oncology. Crit. Rev. Oncol./Hematol.2002, 42, 217–224.10.1016/S1040-8428(01)00217-7Suche in Google Scholar
Vajpayee, V.; Singh, Y. Some homo- and hetero-dinuclear complexes of antimony(III) derived from Schiff base ligands. Phosphorus, Sulfur, Silicon Relat. Elem.2007, 182, 2565–2577.10.1080/10426500701511853Suche in Google Scholar
Viswanathamurthi, P.; Dharmaraj, N.; Natarajan, K. Ruthenium(III) complexes containing monofunctional bidentate Schiff bases. Synth. React. Inorg. Met.-Org. Chem. 2000, 30, 1273–1285.10.1080/00945710009351833Suche in Google Scholar
Vogel, A. I. A Textbook of Quantitative Chemical Analysis, 6th Edition; Longman Group: UK, 2008.Suche in Google Scholar
Yang, N.; Sun, H. Biocoordination chemistry of bismuth: recent advances. Coord. Chem. Rev.2007, 251, 2354–2366.10.1016/j.ccr.2007.03.003Suche in Google Scholar
Yu, G.; Yin, S.; Liu, Y.; Shuai, Z.; Zhu, D. Structures, electronic states, and electroluminescent properties of a zinc(II) 2-(2-hydroxyphenyl)- benzothiazolate complex. J. Am. Chem. Soc.2003, 125, 14816–14824.10.1021/ja0371505Suche in Google Scholar PubMed
©2017 Walter de Gruyter GmbH, Berlin/Boston
This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
Artikel in diesem Heft
- Frontmatter
- Research Articles
- Synthesis and characterization of GeH2Cp*2 and its structural comparison with SiXHCp*2(X=Cl, H) and SnCl2Cp*2
- Facile synthesis of hexagonal strontium ferrite nanostructures and hard magnetic poly carbonate nanocomposite
- Nano-basic silica as an efficient catalyst for the multi-component preparation of pyrano[2,3-d]pyrimidine derivatives
- Selective bulk liquid membrane carrier facilitated transport of Mg2+ over Li+, Na+, K+ and Ca2+ metal ions using naphthaquinone derived redox-switchable ionophores
- Green synthesis and characterization of flower-like PbS and metal-doped nanostructures via hydrothermal method
- Antimony(III) and bismuth(III) complexes containing O- and N-chelating ligands: synthesis, FT-IR, 1H and 13C NMR spectroscopic and mass spectrometric studies
- Synthesis and structure of [Na(15-crown-5)][Ph2P(S)OB(C6F5)3] and [Na(15-crown-5)2][Ph2P(S)O···HO(S)PPh2]
- Short Communication
- Synthesis and structure of the dimericdiorganotinhydroxyphosphinate [t-Bu2Sn(OH)OPPh2O)]2
Artikel in diesem Heft
- Frontmatter
- Research Articles
- Synthesis and characterization of GeH2Cp*2 and its structural comparison with SiXHCp*2(X=Cl, H) and SnCl2Cp*2
- Facile synthesis of hexagonal strontium ferrite nanostructures and hard magnetic poly carbonate nanocomposite
- Nano-basic silica as an efficient catalyst for the multi-component preparation of pyrano[2,3-d]pyrimidine derivatives
- Selective bulk liquid membrane carrier facilitated transport of Mg2+ over Li+, Na+, K+ and Ca2+ metal ions using naphthaquinone derived redox-switchable ionophores
- Green synthesis and characterization of flower-like PbS and metal-doped nanostructures via hydrothermal method
- Antimony(III) and bismuth(III) complexes containing O- and N-chelating ligands: synthesis, FT-IR, 1H and 13C NMR spectroscopic and mass spectrometric studies
- Synthesis and structure of [Na(15-crown-5)][Ph2P(S)OB(C6F5)3] and [Na(15-crown-5)2][Ph2P(S)O···HO(S)PPh2]
- Short Communication
- Synthesis and structure of the dimericdiorganotinhydroxyphosphinate [t-Bu2Sn(OH)OPPh2O)]2
