•  
  •  
 

Al-Bahir Journal for Engineering and Pure Sciences

Abstract

The new ligand N-methyl-N-((((4-nitrophenyl)diazenyl)thio) carbonothioyl) aniline (LS2) was prepared by the reaction of 4-nitrobenzenediazonium salts with a (sodium N-methyl- N-phenyldithiocarbamate), a new ligand containing azo-sulphur linkage. A series of metal ions Sn(II), Sn(IV), Co(II), Ni(II), and Cu(II) were used to prepare metal complexes through reaction of two moles of LS2 ligand with one mole of appropriate metal chloride. The prepared compounds were characterized by CHNS elemental analysis, infrared spectroscopy (FT-IR), 1H NMR-spectroscopy, mass spectroscopy, UV-visible spectroscopy, magnetic susceptibility, and conductivity measurements. Stoichiometry was determined using analytical and spectroscopic information and it was found to be 1:2 (metal to a ligand) for all complexes. The spectral data confirm the coordination of the LS2 ligand with all metal ions through sulfur atoms of dithiocarbamate moiety. Molar conductivity of complexes was measured using DMF as a solvent and it was indicated that all prepared complexes were ionic. According to the results obtained from the elemental analysis and spectral measurements were complexes of Sn(II), Sn(IV) and Co(II) tetrahedral geometry, while the complexes with Ni(II) and Cu(II) had a square planar geometry. The ligand LS2 and its complexes were examined against Staphylococcus aurous bacteria and Escherichia coli bacteria.

References

  1. Soundararajan GSM. A Study on Some Simple and Mixed Ligand N,N-Disubstituted Dithiocarbamates of Thallium(III). Bull Chem Soc Jpn 1984;57:2299e302. URL: http://doi.org/10.1246/bcsj.57.2299
  2. Chatterjee T, Bhadra S, Ranu BC. Transition metal-free procedure for the synthesis of S-aryl dithiocarbamates using aryl diazonium fluoroborate in water at room temperature. Green Chem 2011;13:1837e42. URL: http://doi.org/10.1039/C1GC15136A
  3. Rafin C, Veignie E, Sancholle M, Postel D, Len C, Villa P, et al. Synthesis and antifungal activity of novel bisdithiocarbamate derivatives of carbohydrates against Fusarium oxysporum f. sp. lini. J Agric Food Chem 2000;48:5283e7. URL: http://doi.org/10.1021/jf0004640
  4. Onwudiwe DC, Ajibade PA. Synthesis and crystal structure of Bis(N-alkyl-N-phenyl dithiocarbamato)mercury(II). J Chem Crystallogr 2011;41:980e5. URL: http://doi.org/10.1007/s10870-011-0018-7
  5. JO Adeyemi, Onwudiwe DC, Hosten EC. Organotin(IV) complexes derived from N-ethyl-N-phenyldithiocarbamate: Synthesis, characterization and thermal studies. J Saudi Chem Soc 2018;22:427e38. URL: http://doi.org/10.1016/j.jscs.2017.12.002
  6. JO Adeyemi, Onwudiwe DC. Organotin(IV) dithiocarbamate complexes: Chemistry and biological activity. Molecules 2018;23:1e27. URL: http://doi.org/10.3390/molecules23010027
  7. Tiekink ERT. Tin dithiocarbamates: Applications and structures. Appl Organomet Chem 2008;22:533e50. URL: http://doi.org/10.1002/aoc.1415
  8. Mishra AK, Mishra SB, Kaushik NK. Synthesis, characterization, and antifungal and antibacterial studies of nickel(II) thiodiamine complexes. Russ J Coord Chem Khimiya 2009;35:296e301. URL: http://doi.org/10.1134/S1070328409040055
  9. Kareem A, Nami SAA, Khan MS, Bhat SA, Mirza AU, Laxmi, et al. Self-assembled transition metal dithiocarbamates of pyridine-3-carboxamide: synthesis, spectral characterization, thermal and biological studies. New J Chem 2019;43:4413e24. URL: http://doi.org/10.1039/C8NJ06247D
  10. De Lima GM, Menezes DC, Cavalcanti CA, Dos Santos JAF, Ferreira IP, Paniago EB, et al. Synthesis, characterisation and biological aspects of copper(II) dithiocarbamate complexes, [Cu{S2CNR(CH2CH 2OH)}2], (R ¼ Me, Et, Pr and CH2CH 2OH). J Mol Struct 2011;988:1e8. URL: http://doi.org/10.1016/j.molstruc.2010.11.061
  11. Takahashi S, Sato H, Kubota Y, Utsumi H, Bedford JS. Inhibition of DNA-double strand break repair by antimony compounds. Toxicology 2002;180:249e56. URL: http://doi.org/10.1016/S0300-483X(02)00330-1
  12. Sheng T, Wu X, Lin P, Zhang W, Wang Q, Chen L. Two novel polymeric bismuth(III) complexes with dmit: syntheses and structures of {[Et4N][Bi(dmit)2]}n and {[Et4N]2[Bi2(dmit)4]$ Et2O}n (dmit¼1,3-dithiole-2-thione-4,5-dithiolate). Polyhedron 1999;18:1049e54. URL: http://doi.org/10.1016/S0277-5387(98)00425-9
  13. Niluvanji Matada M, Jathi K, Rangappa MM, Geoffry K, Ravi Kumar S, Nagarajappa RB, et al. A new sulphur containing heterocycles having azo linkage: Synthesis, structural characterization and biological evaluation. J King Saud Univ Sci 2020;32:3313e20. URL: http://doi.org/10.1016/j.jksus.2020.09.025
  14. Halls DJ. The properties of dithiocarbamates A Review. Mikrochim Acta 1969;57:62e77.
  15. Kaul B, Pandeya K. N-monoaryldithiocarbamate cobalt(III) complexes(1). Transit Met Chem 1979;4:112e4.
  16. Prashantha AG, Keshavayya J, Shoukat Ali RA. Synthesis and studies on novel toluic acid-based azo dyes. Rasayan J Chem 2021;14:1635e42.
  17. Aubuchon CM, Rector KD, Holmes W, Fayer MD. Nitro group asymmetric stretching mode lifetimes of molecules used in energetic materials. Chem Phys Lett 1999;299:84e90.
  18. Mahato M, Mukherji S, Van Hecke K, Harms K, Ghosh A, Nayek HP. Mononuclear homoleptic organotin(IV) dithiocarbamates: Syntheses, structures and antimicrobial activities. J Organomet Chem 2017;853:27e34. URL: http://doi.org/10.1016/j.jorganchem.2017.09.016
  19. Hussain S, Ali S, Shahzadi S, Tahir MN, Ramzan S, Shahid M. Synthesis, spectroscopic characterization, X-ray crystal structure and biological activities of homo- and heterobimetallic complexes with potassium-1-dithiocarboxylatopiperidine-4-carboxylate. Polyhedron 2016;119:483e93.
  20. Kilincarslan R, Erdem E, Kocaokutgen H. Synthesis and spectral characterization of some new azo dyes and their metal complexes. Transit Met Chem 2007;32:102e6.
  21. JO Adeyemi, Onwudiwe DC, Singh M. Synthesis, characterization, and cytotoxicity study of organotin(IV) complexes involving different dithiocarbamate groups. J Mol Struct 2019;1179:366e75.
  22. Xiaoqiang X, Wei Z, Zhenping C, Jian Z, Xiulin Z. A novel azo-containing dithiocarbamate used for living radical polymerization of methyl acrylate and styrene. J Polym Sci Part A Polym Chem 2008;46:5626e37.
  23. Onwudiwe DC, Nthwane YB, Ekennia AC, Hosten E. Synthesis, characterization and antimicrobial properties of some mixed ligand complexes of Zn(II) dithiocarbamate with different N-donor ligands. Inorg Chim Acta 2016;447:134e41.
  24. Onwudiwe D, Nthwane Y, Ekennia AC. Synthesis, characterization and antimicrobial properties of some mixed ligand complexes of Zn (II) dithiocarbamate with different N-donor ligands. Inorg Chim Acta 2016;447:134e41.
  25. Hussain Afzal, AlAjmi Mohamed Fahad, Rehman Md Tabish, Amir Samira, Husain Fohad Mabood, Ali Alsalme, Ahmad Siddiqui Maqsood, AAA& RAK. Copper (II) complexes as potential anticancer and Nonsteroidal anti-inflammatory agents: In vitro and in vivo studies. Sci Rep 2019;9:1e17.
  26. Abdul Ghaffar, Khan Naqeebullah, Samiullah IA. View of 67. Biological and electronic transition studies of the previously reported organotin (IV) dithiocarbamates of p-Fluoro-N-methylbenzylaminedithiocarbamate. Pure Appl Biol 2019:672e9.
  27. Mohammad A, Varshney C. A SN. Synthesis, characterization and antifungal activities of 3d-transition metal complexes of 1-acetylpiperazinyldithioc arbamate, M (acpdtc) 2. Spectrochim Acta Part A Mol Biomol Spectrosc 2009;73:20e4.
  28. Mihsen HH, Shareef NK. Synthesis, characterization of mixed-ligand complexes containing 2,2-Bipyridine and 3-aminopropyltriethoxysilane. J Phys Conf Ser 2018;1032.
  29. Shareef NK, Mihsen HH. Synthesis, characterization of mixed-ligand complexes containing 3-aminopropyltriethoxysilane and imidazole. AIP Conf Proc 2019;2144. https://doi.org/10.1063/1.5123058.
  30. Abd El-WahedaM MG, RefatbS S, El-Megharbela M. Metal complexes of antiuralethic drug: Synthesis, spectroscopic characterization and thermal study on allopurinol complexes. J Mol Struct 2008;888:416e29.
  31. Yang T, Qin W. Transition metal manganese (II), nickel (II), copper (II) and zinc (II) complexes of a new Schiff base ligand: synthesis, characterization and antitumor activity studies. Pol J Chem 2006;80:1657e62.
  32. Lever ABP. Inorganic electronic spectroscopy. second ed. Amsterdam: New York Elsevier Pub. Co.; 1968.
  33. Thirumaran S, Ramalingam K. Mixed ligand complexes involving aminoacid dithiocarbamates, substituted phosphines and nickel(II). Transit Met Chem 2000;25:60e2.
  34. Mohammad A, Varshney C, Nami SAA. Synthesis , characterization and antifungal activities of 3d-transition metal complexes of 1-acetylpiperazinyldithioc arbamate , M (acpdtc) 2. Spectrochim Acta Part A Mol Biomol Spectrosc 2009;73:20e4.
  35. Nami SAA, Siddiqi KS. Convenient one-pot synthesis of symmetrical dithiocarbamates. Synth React Inorg Met Chem 2004;34:1581e90. https://doi.org/10.1081/SIM-200026593.
  36. Siddiqi KS, Nami SAA, Lutfullah Chebude Y. Template synthesis of symmetrical transition metal dithiocarbamates. J Braz Chem Soc 2006;17:107e12.
  37. Saha S, Jana S, Gupta S, Ghosh A, Nayek HP. Syntheses, structures and biological activities of square planar Ni(II), Cu(II) complexes. Polyhedron 2016;107:183e9.
  38. Nami SAA, Ullah I, Alam M, Lee DU, Sarikavakli N. Synthesis, characterization, molecular docking and biological studies of self assembled transition metal dithiocarbamates of substituted pyrrole-2-carboxaldehyde. J Photochem Photobiol B Biol 2016;160:392e9.
  39. Ethiraj Sathiyaraj GG, ST. Nickel (II) dithiocarbamate complexes containing the pyrrole moiety for sensing anions and synthesis of nickel sulfide and nickel oxide nanoparticles. New J Chem 2015;39:5336e49.
  40. Andrew FP, Ajibade PA. Synthesis, characterization and anticancer studies of bis(1-phenylpiperazine dithiocarbamato) Cu(II), Zn(II) and Pt(II) complexes: Crystal structures of 1-phenylpiperazine dithiocarbamato-S,S0 zinc(II) and Pt(II). J Mol Struct 2018;1170:24e9.
  41. Yang H, Li L, Song Y, Hou H, Fan Y. Syntheses and characterization of ferrocenylthiocarboxylate-containing coordination compounds for nonlinear optics. J Organomet Chem 2008;693:2624e30.
  42. Nami SAA, Siddiqi KS. Convenient one-pot synthesis of symmetrical dithiocarbamates. Synth React Inorg Met Chem 2004;34:1581e90.
  43. Mihsen HH, Abass SK, Abed Alhasan MT, Hassan ZM, Abbas AK. Synthesis, characterization and antimicrobial activities of mixed ligand complexes of Fe (II), Co(II), Ni(II) and Cu (II) ions derived from imine of benzidine and ophenylenediammine. Iraqi J Sci 2020;61:2762e75.
  44. Geary W. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord Chem Rev 1971;7:81e122.
  45. Hargis L. Analytical chemistry: principles and techniques, vol. 21; 1988.

Share

COinS