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Mixed bismuth(III) complexes with sulfur donor ligands

Studies on synthetic, structural, thermal and biological properties

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Abstract

Mixed bismuth(III) bis(O-alkyldithiocarbonato-S,S′) complexes with dialkyldithiocarbamates have been obtained by two-step one-pot synthesis. These complexes have been characterized by physicochemical (molecular mass determination, melting point and elemental analysis), spectral (UV–Visible, FTIR, far-IR, 1H and 13C NMR), thermal and powder X-ray diffraction studies. It has been observed that both the dithiolato ligands are coordinated via an anisobidentate mode to the central metal atom. Powder XRD analysis indicates that all the complexes are in nanoranged crystallite size (3.1–8.8 nm) and have adopted monoclinic crystal system. Bismuth sulfide (Bi2S3) nanoparticles have been obtained upon thermal decomposition of these complexes. The preparation of bismuth sulfide (Bi2S3) nanoparticles was further confirmed by the help of EDAX analysis of the thermal degradation product. All the synthesized complexes exhibited greater antimicrobial activity than standard antibacterial drug chloramphenicol and antifungal drug terbinafine.

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References

  1. Cotton FA, Wilkinson G, Murillo CA, Bochmann M. Advanced inorganic chemistry. 6th ed. New York: Wiley; 1999.

    Google Scholar 

  2. Levason W, Reid G. Arsenic, antimony, and bismuth. In: Parkin GFR, editor. Comprehensive coordination chemistry II, vol. 3. Amsterdam: Elsevier; 2003. p. 465–544 [Chapter 3.6].

    Chapter  Google Scholar 

  3. Li M, Lu Y, Yang M, Li Y, Zhang L, Xie S. One dodecahedral bismuth(III) complex derived from 2-acetylpyridine N(4)-pyridylthiosemicarbazone: synthesis, crystal structure and biological evaluation. Dalton Trans. 2012;41:12882–7.

    Article  CAS  Google Scholar 

  4. Yang N, Sun HZ. Biocoordination chemistry of bismuth: recent advances. Coord Chem Rev. 2007;251:2354–66.

    Article  CAS  Google Scholar 

  5. Andrews PC, Ferrero RL, Junk PC, Kumar I, Luu Q, Nguyen K, Taylor JW. Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori. Dalton Trans. 2010;39:2861–8.

    Article  CAS  Google Scholar 

  6. Briand GG, Burford N. Bismuth compounds and preparations with biological or medicinal relevance. Chem Rev. 1999;99:2601–57.

    Article  CAS  Google Scholar 

  7. Beales ILP. Efficacy of Helicobacter pylori eradication therapies: a single centre observational study. BMC Gastroenterol. 2001;1:7–16.

    Article  CAS  Google Scholar 

  8. Leonard NM, Wieland LC, Mohan RS. Applications of bismuth(III) compounds in organic synthesis. Tetrahedron. 2002;58:8373–97.

    Article  CAS  Google Scholar 

  9. Carter RH. Insecticidal and fungicidal compositions. US patent 2150759; 1939.

  10. Thorn GD, Ludwig RA. The dithiocarbamates and related compounds. New York: Elsevier Publication; 1962.

    Google Scholar 

  11. Cao SL, Feng YP, Jiang YY, Liu SY, Ding GY, Li RT. Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains. Bioorg Med Chem Lett. 2005;15:1915–7.

    Article  CAS  Google Scholar 

  12. Buac D, Schmitt S, Ventro G, Kona FR, Ping Dou Q. Dithiocarbamate-based coordination compounds as potent proteasome inhibitors in human cancer cells. Mini Rev Med Chem. 2012;12:1193–201.

    Article  CAS  Google Scholar 

  13. Milacic V, Chen D, Ronconi L, Landis-Piwowar KR, Fregona D, Dou QP. A novel anticancer gold(III) dithiocarbamate compound inhibits the activity of a purified 20S proteasome and 26S proteasome in human breast cancer cell cultures and xenografts. Cancer Res. 2006;66:10478–86.

    Article  CAS  Google Scholar 

  14. Müller-Decker K. Interruption of TPA-induced signals by an antiviral and antitumoral xanthate compound: inhibition of a phospholipase c-type reaction. Biochem Biophys Res Commun. 1989;162:198–205.

    Article  Google Scholar 

  15. Amtmann E, Sauer G. Selective killing of tumor cells by xanthates. Cancer Lett. 1987;35:237–44.

    Article  CAS  Google Scholar 

  16. Burrage RH, Menzies JA, Zirk E. Soil treatment with broadcast or band applications of organophosphorus or carbamate insecticides for prevention of wireworm damage to potatoes. J Ecol Entomol. 1967;60:1489–92.

    Article  CAS  Google Scholar 

  17. Cohen SA, Antonis KMD. Applications of amino acid derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate: analysis of feed grains, intravenous solutions and glycoproteins. J Chromatogr A. 1994;661:25–34.

    Article  CAS  Google Scholar 

  18. Kočovský P. Carbamates: a method of synthesis and some synthetic applications. Tetrahedron Lett. 1986;27:5521–4.

    Article  Google Scholar 

  19. Gaur J, Jain S, Bhatia R, Lal A, Kaushik NK. Synthesis and characterization of a novel copolymer of glyoxal dihydrazone and glyoxal dihydrazone bis(dithiocarbamate) and application in heavy metal ion removal from water. J Therm Anal Calorim. 2013;112:1137–43.

    Article  CAS  Google Scholar 

  20. Buchanan RA, Weislogel E, Russell CR, Rist CE. Starch in rubber: zinc starch xanthate in latex masterbatching. Ind Eng Chem Prod Res Dev. 1968;7:155–8.

    Article  CAS  Google Scholar 

  21. Chen K, Grant N, Liang L, Zhang H, Tan B. Synthesis of CO2-philic xanthate-oligo(vinyl acetate)-based hydrocarbon surfactants by RAFT polymerization and their applications on preparation of emulsion-templated materials. Macromolecules. 2010;43:9355–64.

    Article  CAS  Google Scholar 

  22. Dias SC, Brasilino MGA, Pinheiro CD, Souza AG. Metal–sulphur bond enthalpy determination of diethyldithiocarbamate complexes of cadmium and mercury. Thermochim Acta. 1994;241:25–32.

    Article  CAS  Google Scholar 

  23. Carvalho MAP, Airoldi C, Souza AG. Thermochemical features of di-N-propyldithiocabamate chelates of zinc-group elements. J Chem Soc Dalton Trans. 1992;. doi:10.1039/DT9920001235.

    Google Scholar 

  24. Carpenter J, Joshi S, Chauhan HPS. Ethane-1,2-dithiolato bridged (μ2) complexes of bis(N,N-diorganodithiocarbamato-S,S′)antimony(III). J Therm Anal Calorim. 2015;120:1203–15.

    Article  CAS  Google Scholar 

  25. Kropidłowska AM, Chojnacki J, Strankowski M, Fahmi A, Gazda M, Becker B. Cadmium complex possessing simultaneously silanethiolato and dithiocarbamato-ligands. A novel single-source precursor of cadmium sulfide. J Therm Anal Calorim. 2014;118:993–1001.

    Article  Google Scholar 

  26. Zhang Z, Cui ZL. Nanotechnology and nanomaterial. Beijing: National Defence Industry Publication; 2000.

    Google Scholar 

  27. Lu Q, Gao F, Komarneni S. Biomolecule-assisted synthesis of highly ordered snow flake like structures of bismuth sulfide nanorods. J Am Chem Soc. 2004;126:54–5.

    Article  CAS  Google Scholar 

  28. Liu L, Wang L, Yin H, Li Y, He X. The preparation and application of bismuth(III) ion-selective electrode based on nanoparticles of bismuth sulfide. Anal Lett. 2006;39:879–90.

    Article  CAS  Google Scholar 

  29. Chauhan HPS, Shaik NM, Singh UP. Synthesis, spectroscopic characterization and in vitro studies of antimicrobial activity of bis(diorganodithiocarbamato) organodithiocarbonatobismuth(III) complexes. Appl Organomet Chem. 2006;20:142–8.

    Article  CAS  Google Scholar 

  30. Chauhan HPS, Joshi S, Bakshi A, Carpenter J. Structural investigation on toluene-3,4-dithiolatoantimony(III) alkyldithiocarbonate complexes: thermal, powder XRD and biological studies. New J Chem. 2015;39:2279–88.

    Article  CAS  Google Scholar 

  31. Chauhan HPS, Bakshi A, Bhatiya S. Synthesis, spectroscopic characterization and antibacterial activity of antimony(III) bis(dialkyldithiocarbamato)alkyldithiocarbonates. Spectrochim Acta A. 2011;81:417–23.

    Article  CAS  Google Scholar 

  32. Koh YW, Lai CS, Du AY, Tiekink ERT, Loh KP. Growth of bismuth sulfide nanowire using bismuth trisxanthate single source precursors. Chem Mater. 2003;15:4544–54.

    Article  CAS  Google Scholar 

  33. Riddick JA, Bunger WB. Techniques of chemistry (organic solvents), vol. 2. New York: Wiley Interscience; 1970.

    Google Scholar 

  34. Magaldi S, Mata-Essayag S, De Capriles CH, Perez C, Colella MT, Olaizola C, Ontiveros Y. Well diffusion for antifungal susceptibility testing. Int J Infect Dis. 2004;8:39–45.

    Article  CAS  Google Scholar 

  35. Boyanova L, Gergova G, Nikolov R, Derejian S, Lazarova E, Katsarov N, Mitov I, Krastev Z. Activity of Bulgarian propolis against 94 helicobacter pylori strains in vitro by agar-well diffusion, agar dilution and disc diffusion methods. J Med Microbiol. 2005;54:481–3.

    Article  Google Scholar 

  36. Xiao G, Dong Q, Wang Y, Sui Y, Ning J, Liu Z, Tian W, Liu B, Zoua G, Zou B. One-step solution synthesis of bismuth sulfide (Bi2S3) with various hierarchical architectures and their photoresponse properties. RSC Adv. 2012;2:234–40.

    Article  CAS  Google Scholar 

  37. Chauhan HPS, Joshi S, Carpenter J. Synthetic, spectral, thermal and powder X-ray diffraction studies of bis(O-alkyldithiocarbonato-S,S′) antimony(III) dialkyldithiocarbamates. Spectrochim Acta A. 2015;136:1626–34.

    Article  CAS  Google Scholar 

  38. Manoussakis GE, Tsipis CA. Preparation and study of some arsenic and antimony tris dithiocarbamates. J Inorg Nucl Chem. 1973;35:743–50.

    Article  CAS  Google Scholar 

  39. Chauhan HPS, Bakshi A. Synthetic, spectroscopic, thermal, and structural studies of antimony(III) bis(pyrrolidinedithiocarbamato)alkyldithiocarbonates. J Therm Anal Calorim. 2011;105:937–46.

    Article  CAS  Google Scholar 

  40. Chauhan HPS, Carpenter J, Joshi S. Mixed bis(morpholine-4-dithiocarbamato-S, S′) antimony(III) complexes: synthesis, characterization and biological studies. Appl Organomet Chem. 2014;28:605–13.

    Article  CAS  Google Scholar 

  41. Chauhan HPS, Singh RK. Synthesis and characterization of bismuth(III) bis(dialkyldithiophosphate) alkyldithiocarbonate. Synth React Inorg Met-Org Chem. 2000;30(7):1211–9.

    Article  CAS  Google Scholar 

  42. Chauhan HPS, Shaik NM, Singh UP. Synthetic, spectroscopic and antimicrobial studies of bis(dialkyldithiocarbamato)diorganodithiophosphatobismuth(III) complexes. Appl Organomet Chem. 2005;19:1132–9.

    Article  CAS  Google Scholar 

  43. Bailey JHE, Drake JE, Khasrou LN, Yang J. Synthesis and spectroscopic characterization of O-alkyl dithiocarbonate (xanthate) derivatives of dimethyl- and diphenyltellurium(IV) crystal structures of Me2Te[S2COEt]2 and Ph2Te[S2COEt]2. Inorg Chem. 1995;34:124–33.

    Article  CAS  Google Scholar 

  44. Van Gaal HLM, Diesveld JW, Pijpers FW, Van Der Linden JGM. 13C NMR spectra of dithiocarbamates chemical shifts, carbon–nitrogen stretching vibration frequencies, and p bonding in the NCS2 fragment. Inorg Chem. 1979;18:3251–60.

    Article  Google Scholar 

  45. Cullity BD. Elements of X-ray diffraction. Reading: Addison-Wesley Publishing Company; 1958.

    Google Scholar 

  46. Klug HP, Alexander LE. X-ray diffraction procedures for polycrystalline and amorphous materials. New York: Wiley; 1974.

    Google Scholar 

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Acknowledgements

Financial assistance in the form of a research project by Madhya Pradesh Council of Science & Technology (MPCST, File No.: A/R&D/RP–02/2012/199) is gratefully acknowledged. We are thankful to Sophisticated Analytical Instrumentation Facility (SAIF) of Panjab University, Chandigarh (for spectral and elemental study), IISER, Bhopal (for thermal study), UGC–DAE Consortium for Scientific Research (for powder XRD and EDAX analyses) and Holkar Science College, Indore (for biological studies).

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Correspondence to H. P. S. Chauhan.

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Chauhan, H.P.S., Joshi, S. & Carpenter, J. Mixed bismuth(III) complexes with sulfur donor ligands. J Therm Anal Calorim 124, 117–130 (2016). https://doi.org/10.1007/s10973-015-5164-1

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