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One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes

Year 2020, Volume: 2 Issue: 2, 81 - 86, 29.12.2020
https://doi.org/10.51435/turkjac.813792

Abstract

In this work, the synthesis of thiosemicarbazones (I-V) was carried out using one pot method, multicomponent and catalyst-free reaction of cyclohexyl isothiocyanate, hydrazine monohydrate and 5-substituted-2-furancarbaldehydes in good yields. The chemical structures of 5-substituted-2-furancarbaldehyde thiosemicarbazones were eludicated using UV‐Vis, IR, 1H NMR, 13C NMR, mass spectra, and elemental analysis. Also, the reaction of NiCl2.6H2O with thiosemicarbazones in 1:2 molar ratio by refluxing gave the nickel (II) complexes (Ia-Va) as binuclear and their structures characterized by UV-Vis, IR, and elemental analysis.

Supporting Institution

Scientific Research Projects Governing Unit Council of Scientific Research Projects

Project Number

Grant no. FEF.08.10

Thanks

This work was supported by Scientific Research Projects Governing Unit Council of Scientific Research Projects (Grant no. FEF.08.10), Gaziantep, Turkey.

References

  • [1] T.S. Lobana, R. Sharma, G. Bawa, S. Khanna, Bonding and structure trends of thiosemicarbazone derivatives of metals-An overview, Coord Chem Rev, 253, 2009, 977-1055.
  • [2] S. Savir, Z.J. Wei, J.W.K. Liew, I. Vythilingam, Y.A.L. Lim, H.M. Saad, K.S. Sim, K.W. Tan, Synthesis, cytotoxicity and antimalarial activities of thiosemicarbazones and their nickel (II) complexes, J Mol Struct, 1211, 2020, 128090.
  • [3] C. Bonaccorso, T. Marzo, D. La Mendola, Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review, Pharmaceuticals, 13(4), 2020, 1-19.
  • [4] A.l. Matesanz, P. Albacete, P. Souza, Synthesis and characterization of a new bioactive mono(thiosemicarbazone) ligand based on 3,5-diacetyl-1,2,4-triazol diketone and its palladium and platinum complexes, Polyhedron 109, 2016, 161-165.
  • [5] T.P. Stanojkovic, D. Kovala-Demertzi, A. Primikyri, I. Garcia-Santos, A. Castineiras, Z.Juranic, M.A. Demertzis, Zinc(II) complexes of 2-acetyl pyridine 1-(4-fluorophenyl)-piperazinyl thiosemicarbazone: Synthesis, spectroscopic study and crystal structures– Potential anticancer drugs J. Inorg. Biochem. 104 (2010) 467- 476.
  • [6] V.M. Leovac, S.B. Novakovic, G.A. Bogdanovic, M.D. Joksovic, K.M. Szecsenyi, V.I. Cesljevic, Transition metal complexes with thiosemicarbazide-based ligands. Part LVI: Nickel(II) complex with 1,3-diphenylpyrazole-4-carboxaldehyde thiosemicarbazone and unusually deformed coordination geometry, Polyhedron, 26, 2007, 3783-3792.
  • [7] Z. Piri, Z. Moradi-Shoeili, A. Assoud, Ultrasonic assisted synthesis, crystallographic, spectroscopic studies and biological activity of three new Zn(II), Co(II) and Ni(II) thiosemicarbazone complexes as precursors for nano-metal oxides Inorg Chim Acta, 484, 2019, 338- 346.
  • [8] N.P. Prajapati, H.D. Patel, Novel thiosemicarbazone derivatives and their metal complexes: Recent development, Synthetic Commun Rev, 2019, 1-38.
  • [9] A. Karaküçük-İyidoğan, D. Taşdemir, E.E. Oruç-Emre, J. Balzarini, Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities, Eur J Med Chem, 46, 2011, 5616-5624.
  • [10] A. Akbari, H. Ghateazadeh, R. Takjoo, B. Sadeghi-Nejad, M. Mehrvar, J.T. Mague, Synthesis & crystal structures of four new biochemical active Ni(II) complexes of thiosemicarbazone and isothiosemicarbazone-based ligands: In vitro antimicrobial study, J Mol Struct 181, 2019, 287-294.
  • [11] E. Bozgeyik, D. Taşdemir-Kahraman, K. Arman, İ. Bozgeyik, A. Karaküçük-İyidoğan, E.A. Çakmak, Novel thiosemicarbazone derivative 17B interferes with the cell cycle progression and induce apoptosis through modulating downstream signaling pathways, Gene Reports, 18, 2020, 100578.
  • [12] A. Karaküçük-İyidoğan, Z. Mercan, E.E. Oruç-Emre, D. Taşdemir, D. İşler, İ.H. Kılıç, M. Özaslan, Synthesis, characterization, and biological evaluation of some novel thiosemicarbazones as possible antibacterial and antioxidant agents, Phosphorous, Sulfur and Silicon and Related Elements, 189, 2014, 661-673.
  • [13] M.T. Shehzad, A.Imranb, G.S.S. Njateng, A. Hameed , M. Islam , M. al-Rashida, M. Uroos, A. Asari, Z. Shafiq, J. Iqbal, Benzoxazinone-thiosemicarbazones as antidiabetic leads via aldose reductase inhibition: Synthesis, biological screening and molecular docking study, Bioorg Chem, article in press, doi: 10.1016/j.bioorg.2018.12.006.
  • [14] H.B. Shawish, W.Y. Wong, Y.L. Wong, S.W. Loh, C.Y. Looi, P. Hassandarvish, A.Y.L. Phan, W.F. Wong, H. Wang, I.C. Paterson, C.K. Ea, M.R. Mustafa, M.J. Maah, Nickel(II) Complex of Polyhydroxybenzaldehyde N4- Thiosemicarbazone Exhibits Anti-Inflammatory Activity by Inhibiting NF-kB Transactivation, PLoS One, 9(6), 2014, e100933.
  • [15] J.S. Casas, M.S. Garcia-Tasende, J. Sordo, Main group metal complexes of semicarbazones and thiosemicarbazones. A structural review, Coord Chem Rev, 209, 2000, 197-261.
  • [16] V.V. Bon, S.I. Orysyk, V.I. Pekhnyo, S.V. Volkov, Square-planer 1:2 Ni(II) and Pd(II) complexes with different coordination mode of salicylaldehyd (4)-phenylthiosemicarbazone: synthesis, structure and spectral properties, J Mol Struct, 984, 2010, 15-22.
  • [17] E. Pahontu, C. Paraschivescu, D.-C. Ilieş, D. Poirier, C. Oprean, V. Paunescu, A. Gulea, T. Roşu, O. Bratu, Synthesis and characterization of novel Cu(II), Pd(II) and Pt(II) complexes with 8-ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one thiosemicarbazone: antimicrobial and in vitro antiproliferative activity, Molecules, 21, 674, 2016, 1-18.
  • [18] I. Pal, F. Basuli, S. Bhattacharya, Thiosemicarbazone complexes of the platinum metals. A story of variable coordination modes, Proc Indian Acad Sci (Chem Sci), 114, 2002, 255-268.
  • [19] S. Cunha, T.L. da Silva, One-pot and catalyst-free synthesis of thiosemicarbazones via multicomponent coupling reactions, Tetrahedron Lett, 50, 2009, 2090-2093.
  • [20] D. Taşdemir, A. Karaküçük-İyidoğan, M. Ulaşlı, T. Taşkın-Tok, E.E. Oruç-Emre, H. Bayram, Synthesis, molecular modeling, and biological evaluation of novel chiral thiosemicarbazone derivatives as potent anticancer agents, Chirality, 27, 2015, 177-188.
  • [21] A. Karaküçük-İyidoğan, B. Aydınöz, T. Taşkın-Tok, E.E. Oruç-Emre, J. Balzarini, Synthesis, biological evaluation and ligand based pharmacophore modeling of new aromatic thiosemicarbazones as potential anticancer agents, Pharm Chem J, 53(2), 2019, 139-149.
  • [22] M.-H. Shih, Y.-Y. Xu, Y.-S. Yang, T.-T. Lin, Syntheses of Nickel (II) complexes from novel semicarbazone ligands with chloroformylarylhydrazine, benzimidazole and salicylaldehyde moieties, Molecules, 20, 2015, 5184-5201.
  • [23] D. Bahl, F. Athar, M.B.P. Soares, M.S. de Sa, D.R.M. Moreira, R.M. Srivastava, A.C.L. Leite, A. Azam, Structure–activity relationships of mononuclear metal-thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities, Bioorg Med Chem, 18, 2010, 6857-6864.
  • [24] E.M. Jouad, A. Riou, M. Allain, M.A. Khan, G.M. Bouet, Synthesis, structural and spectral studies of 5-methyl 2-furaldehyde thiosemicarbazone and its Co, Ni, Cu and Cd complexes, Polyhedron, 20, 2001, 67-74.
  • [25] E. Viñuelas-Zahínos, F. Luna-Giles, P. Torres-García, M.C. Fernández-Calderón, Co(III), Ni(II), Zn(II) and Cd(II) complexes with 2-acetyl-2-thiazoline thiosemicarbazone: synthesis, characterization, X-ray structures and antibacterial activity, Eur J Med Chem, 46, 2011, 150-159.
  • [26] M.B. Ferrari, S. Capacchi, F. Bisceglie, G. Pelosi, P. Tarasconi, Synthesis and characterization of square planar nickel(II) complexes with p-fluorobenzaldehyde thiosemicarbazone derivatives, Inorg Chim Acta, 312, 2001, 81-87.
  • [27] Y. Li, Z.-Y. Yang, J.-C. Wu, Synthesis, crystal structures, biological activities and fluorescence studies of transition metal complexes with 3-carbaldehyde chromone thiosemicarbazone, Eur J Med Chem, 45, 2010, 5692-5701.
  • [28] L. Latheef, M.R.P. Kurup, Spectral and structural studies of nickel(II) complexes of salicylaldehyde 3-azacyclothiosemicarbazones, Polyhedron, 27, 2008, 35-43.
  • [29] U.M. Osman, S. Silvarajoo, K.H. Kamarudin, M.I.M. Tahir, K.H. Chong, Ni(II) complex containing a thiosemicarbazone ligand: Synthesis, spectroscopy, single-crystal X-ray crystallographic and conductivity studies, J Mol Struct, 2020, article in press, doi: 10.1016/j.molstruc.2020.128994.
  • [30] M.C. Rodríguez-Argüelles, P. Tourón-Touceda, R. Cao, A.M. García-Deibe, P. Pelagatti, C. Pelizzi, F. Zani, Complexes of 2-acetyl-γ-butyrolactone and 2-furancarbaldehyde thiosemicarbazones: Antibacterial and antifungal activity, J Inorg Biochem, 103, 2009, 35-42.
  • [31] A.H. Pathan, R.P. Bakale, G.N. Naik, C.S. Frampton, K.B. Gudasi, Synthesis, crystal structure, redox behavior and comprehensive studies on DNA binding and cleavage properties of transition metal complexes of a fluorosubstituted thiosemicarbazone derived from ethyl pyruvate, Polyhedron, 34, 2012, 149-156.
Year 2020, Volume: 2 Issue: 2, 81 - 86, 29.12.2020
https://doi.org/10.51435/turkjac.813792

Abstract

Project Number

Grant no. FEF.08.10

References

  • [1] T.S. Lobana, R. Sharma, G. Bawa, S. Khanna, Bonding and structure trends of thiosemicarbazone derivatives of metals-An overview, Coord Chem Rev, 253, 2009, 977-1055.
  • [2] S. Savir, Z.J. Wei, J.W.K. Liew, I. Vythilingam, Y.A.L. Lim, H.M. Saad, K.S. Sim, K.W. Tan, Synthesis, cytotoxicity and antimalarial activities of thiosemicarbazones and their nickel (II) complexes, J Mol Struct, 1211, 2020, 128090.
  • [3] C. Bonaccorso, T. Marzo, D. La Mendola, Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review, Pharmaceuticals, 13(4), 2020, 1-19.
  • [4] A.l. Matesanz, P. Albacete, P. Souza, Synthesis and characterization of a new bioactive mono(thiosemicarbazone) ligand based on 3,5-diacetyl-1,2,4-triazol diketone and its palladium and platinum complexes, Polyhedron 109, 2016, 161-165.
  • [5] T.P. Stanojkovic, D. Kovala-Demertzi, A. Primikyri, I. Garcia-Santos, A. Castineiras, Z.Juranic, M.A. Demertzis, Zinc(II) complexes of 2-acetyl pyridine 1-(4-fluorophenyl)-piperazinyl thiosemicarbazone: Synthesis, spectroscopic study and crystal structures– Potential anticancer drugs J. Inorg. Biochem. 104 (2010) 467- 476.
  • [6] V.M. Leovac, S.B. Novakovic, G.A. Bogdanovic, M.D. Joksovic, K.M. Szecsenyi, V.I. Cesljevic, Transition metal complexes with thiosemicarbazide-based ligands. Part LVI: Nickel(II) complex with 1,3-diphenylpyrazole-4-carboxaldehyde thiosemicarbazone and unusually deformed coordination geometry, Polyhedron, 26, 2007, 3783-3792.
  • [7] Z. Piri, Z. Moradi-Shoeili, A. Assoud, Ultrasonic assisted synthesis, crystallographic, spectroscopic studies and biological activity of three new Zn(II), Co(II) and Ni(II) thiosemicarbazone complexes as precursors for nano-metal oxides Inorg Chim Acta, 484, 2019, 338- 346.
  • [8] N.P. Prajapati, H.D. Patel, Novel thiosemicarbazone derivatives and their metal complexes: Recent development, Synthetic Commun Rev, 2019, 1-38.
  • [9] A. Karaküçük-İyidoğan, D. Taşdemir, E.E. Oruç-Emre, J. Balzarini, Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities, Eur J Med Chem, 46, 2011, 5616-5624.
  • [10] A. Akbari, H. Ghateazadeh, R. Takjoo, B. Sadeghi-Nejad, M. Mehrvar, J.T. Mague, Synthesis & crystal structures of four new biochemical active Ni(II) complexes of thiosemicarbazone and isothiosemicarbazone-based ligands: In vitro antimicrobial study, J Mol Struct 181, 2019, 287-294.
  • [11] E. Bozgeyik, D. Taşdemir-Kahraman, K. Arman, İ. Bozgeyik, A. Karaküçük-İyidoğan, E.A. Çakmak, Novel thiosemicarbazone derivative 17B interferes with the cell cycle progression and induce apoptosis through modulating downstream signaling pathways, Gene Reports, 18, 2020, 100578.
  • [12] A. Karaküçük-İyidoğan, Z. Mercan, E.E. Oruç-Emre, D. Taşdemir, D. İşler, İ.H. Kılıç, M. Özaslan, Synthesis, characterization, and biological evaluation of some novel thiosemicarbazones as possible antibacterial and antioxidant agents, Phosphorous, Sulfur and Silicon and Related Elements, 189, 2014, 661-673.
  • [13] M.T. Shehzad, A.Imranb, G.S.S. Njateng, A. Hameed , M. Islam , M. al-Rashida, M. Uroos, A. Asari, Z. Shafiq, J. Iqbal, Benzoxazinone-thiosemicarbazones as antidiabetic leads via aldose reductase inhibition: Synthesis, biological screening and molecular docking study, Bioorg Chem, article in press, doi: 10.1016/j.bioorg.2018.12.006.
  • [14] H.B. Shawish, W.Y. Wong, Y.L. Wong, S.W. Loh, C.Y. Looi, P. Hassandarvish, A.Y.L. Phan, W.F. Wong, H. Wang, I.C. Paterson, C.K. Ea, M.R. Mustafa, M.J. Maah, Nickel(II) Complex of Polyhydroxybenzaldehyde N4- Thiosemicarbazone Exhibits Anti-Inflammatory Activity by Inhibiting NF-kB Transactivation, PLoS One, 9(6), 2014, e100933.
  • [15] J.S. Casas, M.S. Garcia-Tasende, J. Sordo, Main group metal complexes of semicarbazones and thiosemicarbazones. A structural review, Coord Chem Rev, 209, 2000, 197-261.
  • [16] V.V. Bon, S.I. Orysyk, V.I. Pekhnyo, S.V. Volkov, Square-planer 1:2 Ni(II) and Pd(II) complexes with different coordination mode of salicylaldehyd (4)-phenylthiosemicarbazone: synthesis, structure and spectral properties, J Mol Struct, 984, 2010, 15-22.
  • [17] E. Pahontu, C. Paraschivescu, D.-C. Ilieş, D. Poirier, C. Oprean, V. Paunescu, A. Gulea, T. Roşu, O. Bratu, Synthesis and characterization of novel Cu(II), Pd(II) and Pt(II) complexes with 8-ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one thiosemicarbazone: antimicrobial and in vitro antiproliferative activity, Molecules, 21, 674, 2016, 1-18.
  • [18] I. Pal, F. Basuli, S. Bhattacharya, Thiosemicarbazone complexes of the platinum metals. A story of variable coordination modes, Proc Indian Acad Sci (Chem Sci), 114, 2002, 255-268.
  • [19] S. Cunha, T.L. da Silva, One-pot and catalyst-free synthesis of thiosemicarbazones via multicomponent coupling reactions, Tetrahedron Lett, 50, 2009, 2090-2093.
  • [20] D. Taşdemir, A. Karaküçük-İyidoğan, M. Ulaşlı, T. Taşkın-Tok, E.E. Oruç-Emre, H. Bayram, Synthesis, molecular modeling, and biological evaluation of novel chiral thiosemicarbazone derivatives as potent anticancer agents, Chirality, 27, 2015, 177-188.
  • [21] A. Karaküçük-İyidoğan, B. Aydınöz, T. Taşkın-Tok, E.E. Oruç-Emre, J. Balzarini, Synthesis, biological evaluation and ligand based pharmacophore modeling of new aromatic thiosemicarbazones as potential anticancer agents, Pharm Chem J, 53(2), 2019, 139-149.
  • [22] M.-H. Shih, Y.-Y. Xu, Y.-S. Yang, T.-T. Lin, Syntheses of Nickel (II) complexes from novel semicarbazone ligands with chloroformylarylhydrazine, benzimidazole and salicylaldehyde moieties, Molecules, 20, 2015, 5184-5201.
  • [23] D. Bahl, F. Athar, M.B.P. Soares, M.S. de Sa, D.R.M. Moreira, R.M. Srivastava, A.C.L. Leite, A. Azam, Structure–activity relationships of mononuclear metal-thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities, Bioorg Med Chem, 18, 2010, 6857-6864.
  • [24] E.M. Jouad, A. Riou, M. Allain, M.A. Khan, G.M. Bouet, Synthesis, structural and spectral studies of 5-methyl 2-furaldehyde thiosemicarbazone and its Co, Ni, Cu and Cd complexes, Polyhedron, 20, 2001, 67-74.
  • [25] E. Viñuelas-Zahínos, F. Luna-Giles, P. Torres-García, M.C. Fernández-Calderón, Co(III), Ni(II), Zn(II) and Cd(II) complexes with 2-acetyl-2-thiazoline thiosemicarbazone: synthesis, characterization, X-ray structures and antibacterial activity, Eur J Med Chem, 46, 2011, 150-159.
  • [26] M.B. Ferrari, S. Capacchi, F. Bisceglie, G. Pelosi, P. Tarasconi, Synthesis and characterization of square planar nickel(II) complexes with p-fluorobenzaldehyde thiosemicarbazone derivatives, Inorg Chim Acta, 312, 2001, 81-87.
  • [27] Y. Li, Z.-Y. Yang, J.-C. Wu, Synthesis, crystal structures, biological activities and fluorescence studies of transition metal complexes with 3-carbaldehyde chromone thiosemicarbazone, Eur J Med Chem, 45, 2010, 5692-5701.
  • [28] L. Latheef, M.R.P. Kurup, Spectral and structural studies of nickel(II) complexes of salicylaldehyde 3-azacyclothiosemicarbazones, Polyhedron, 27, 2008, 35-43.
  • [29] U.M. Osman, S. Silvarajoo, K.H. Kamarudin, M.I.M. Tahir, K.H. Chong, Ni(II) complex containing a thiosemicarbazone ligand: Synthesis, spectroscopy, single-crystal X-ray crystallographic and conductivity studies, J Mol Struct, 2020, article in press, doi: 10.1016/j.molstruc.2020.128994.
  • [30] M.C. Rodríguez-Argüelles, P. Tourón-Touceda, R. Cao, A.M. García-Deibe, P. Pelagatti, C. Pelizzi, F. Zani, Complexes of 2-acetyl-γ-butyrolactone and 2-furancarbaldehyde thiosemicarbazones: Antibacterial and antifungal activity, J Inorg Biochem, 103, 2009, 35-42.
  • [31] A.H. Pathan, R.P. Bakale, G.N. Naik, C.S. Frampton, K.B. Gudasi, Synthesis, crystal structure, redox behavior and comprehensive studies on DNA binding and cleavage properties of transition metal complexes of a fluorosubstituted thiosemicarbazone derived from ethyl pyruvate, Polyhedron, 34, 2012, 149-156.
There are 31 citations in total.

Details

Primary Language English
Subjects Analytical Chemistry
Journal Section Research Articles
Authors

Ayşegül İyidoğan 0000-0002-8088-6010

Emine Elçin Oruç-emre 0000-0001-6840-9660

Ülkü Çakır This is me 0000-0001-8429-3098

Project Number Grant no. FEF.08.10
Publication Date December 29, 2020
Submission Date October 21, 2020
Acceptance Date November 21, 2020
Published in Issue Year 2020 Volume: 2 Issue: 2

Cite

APA İyidoğan, A., Oruç-emre, E. E., & Çakır, Ü. (2020). One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes. Turkish Journal of Analytical Chemistry, 2(2), 81-86. https://doi.org/10.51435/turkjac.813792
AMA İyidoğan A, Oruç-emre EE, Çakır Ü. One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes. TurkJAC. December 2020;2(2):81-86. doi:10.51435/turkjac.813792
Chicago İyidoğan, Ayşegül, Emine Elçin Oruç-emre, and Ülkü Çakır. “One Pot Synthesis and Spectral Characterization of 5-Substitutedfuran-2-Carbaldehyde N4-Cyclohexyl Thiosemicarbazones and Their Ni(II) Complexes”. Turkish Journal of Analytical Chemistry 2, no. 2 (December 2020): 81-86. https://doi.org/10.51435/turkjac.813792.
EndNote İyidoğan A, Oruç-emre EE, Çakır Ü (December 1, 2020) One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes. Turkish Journal of Analytical Chemistry 2 2 81–86.
IEEE A. İyidoğan, E. E. Oruç-emre, and Ü. Çakır, “One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes”, TurkJAC, vol. 2, no. 2, pp. 81–86, 2020, doi: 10.51435/turkjac.813792.
ISNAD İyidoğan, Ayşegül et al. “One Pot Synthesis and Spectral Characterization of 5-Substitutedfuran-2-Carbaldehyde N4-Cyclohexyl Thiosemicarbazones and Their Ni(II) Complexes”. Turkish Journal of Analytical Chemistry 2/2 (December 2020), 81-86. https://doi.org/10.51435/turkjac.813792.
JAMA İyidoğan A, Oruç-emre EE, Çakır Ü. One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes. TurkJAC. 2020;2:81–86.
MLA İyidoğan, Ayşegül et al. “One Pot Synthesis and Spectral Characterization of 5-Substitutedfuran-2-Carbaldehyde N4-Cyclohexyl Thiosemicarbazones and Their Ni(II) Complexes”. Turkish Journal of Analytical Chemistry, vol. 2, no. 2, 2020, pp. 81-86, doi:10.51435/turkjac.813792.
Vancouver İyidoğan A, Oruç-emre EE, Çakır Ü. One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes. TurkJAC. 2020;2(2):81-6.