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Dioxomolybdenum(VI) complexes of ONN chelating thiosemicarbazones: Crystallographic and spectroscopic (UV, IR and NMR) studies

Yıl 2021, Cilt 8, Sayı 4, 1275 - 1300, 30.11.2021
https://doi.org/10.18596/jotcsa.989318

Öz

Four new cis-dioxomolybdenum(VI) complexes of the closed formula [MoO2(L)CH3OH] have been obtained by the condensation of bis(acetylacetonato)dioxomolybdenum(VI) with S-allyl/propyl thiosemicarbazones in methanol. The compounds were identified with elemental analysis, and molecular characterization by UV-Vis, FT-IR, 1H-NMR and 13C-NMR spectroscopies. Also, crystal structures of 1 and 2 were resolved by X-ray diffraction analysis. The single crystal studies indicated a distorted octahedral geometry for complexes. It was noticed that 1 crystallized in the monoclinic P21/c space group with Z=4, while 2 crystallized in tricilinic P-1 space group with Z=2. The O=Mo=O angles of 105.68(8)° (for 1) and 105.96(7)° (for 2) indicated the cis-dioxomolybdenum structure. The spectroscopic and crystallographic studies show that the thiosemicarbazone ligands are bound to cis-MoO22+ moiety as ONN tridentate agent and the 6th coordinated position of the molybdenum is located by the methanol molecule.

Kaynakça

  • 1. Leovac V, Gerbeleu N, Canic V. Coordination compounds of cobalt (III), chromium (III), and vanadium (III) with salicylaldehyde S-methylthiosemicarbazone. Russ J Inorg Chem. 1982;27:514–7.
  • 2. Nehar OK, Mahboub R, Louhibi S, Roisnel T, Aissaoui M. New thiosemicarbazone Schiff base ligands: Synthesis, characterization, catecholase study and hemolytic activity. Journal of Molecular Structure. 2020 Mar;1204:127566.
  • 3. Behnisch R, Mietzsch F, Schmidt H. Chemical Studies on Thiosemicarbazones with Particular Reference to Antituberculous Acitivity. American review of tuberculosis. 1950;61(1):1–7.
  • 4. Plech T, Wujec M, Siwek A, Kosikowska U, Malm A. Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety. European Journal of Medicinal Chemistry. 2011 Jan;46(1):241–8.
  • 5. Kesel AJ. Broad-spectrum antiviral activity including human immunodeficiency and hepatitis C viruses mediated by a novel retinoid thiosemicarbazone derivative. European Journal of Medicinal Chemistry. 2011 May;46(5):1656–64.
  • 6. Li MX, Chen CL, Zhang D, Niu JY, Ji BS. Mn(II), Co(II) and Zn(II) complexes with heterocyclic substituted thiosemicarbazones: Synthesis, characterization, X-ray crystal structures and antitumor comparison. European Journal of Medicinal Chemistry. 2010 Jul;45(7):3169–77.
  • 7. Rodríguez-Argüelles MC, López-Silva EC, Sanmartín J, Pelagatti P, Zani F. Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: Inhibitory activity against fungi and bacteria. Journal of Inorganic Biochemistry. 2005 Nov;99(11):2231–9.
  • 8. Saswati, Dinda R, Schmiesing CS, Sinn E, Patil YP, Nethaji M, et al. Mixed-ligand nickel(II) thiosemicarbazone complexes: Synthesis, characterization and biological evaluation. Polyhedron. 2013 Feb;50(1):354–63.
  • 9. Viñuelas-Zahínos E, Luna-Giles F, Torres-García P, Fernández-Calderón MC. Co(III), Ni(II), Zn(II) and Cd(II) complexes with 2-acetyl-2-thiazoline thiosemicarbazone: Synthesis, characterization, X-ray structures and antibacterial activity. European Journal of Medicinal Chemistry. 2011 Jan;46(1):150–9.
  • 10. Chen J, Huang Y, Liu G, Afrasiabi Z, Sinn E, Padhye S, et al. The cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells. Toxicology and Applied Pharmacology. 2004 May;197(1):40–8.
  • 11. Afrasiabi Z. Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line, T47D. Journal of Inorganic Biochemistry. 2003 Jul 1;95(4):306–14.
  • 12. Eğlence-Bakır S, Sacan O, Şahin M, Yanardag R, Ülküseven B. Dioxomolybdenum(VI) complexes with 3-methoxy salicylidene-N-alkyl substituted thiosemicarbazones. Synthesis, characterization, enzyme inhibition and antioxidant activity. Journal of Molecular Structure. 2019 Oct;1194:35–41.
  • 13. Eğlence-Bakır S. New nickel(II) complexes containing N2O2 donor thiosemicarbazones: Synthesis, characterization and antioxidant properties. Journal of Molecular Structure. 2021 Dec;1246:131121.
  • 14. Bakkar MS, Siddiqi MY, Monshi MS. Preparation and Investegation of the Bonding Mode in the Complexes of Pt(II) with Thiosemicarbazone Ligands. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 2003 Jan 8;33(7):1157–69.
  • 15. Ren P, Liu T, Qin J, Chen C. Synthesis, Crystal Structure, Spectroscopy and Calculated First-Order Molecular Hyperpolarizability of a New Square-pyramidal Complex Zn(DMABT)(acac) 2. Journal of Coordination Chemistry. 2003 Jan 1;56(2):125–32.
  • 16. Sankaraperumal A, Karthikeyan J, Shetty AN, Lakshmisundaram R. Nickel(II) complex of p-[N,N-bis(2-chloroethyl)amino]benzaldehyde-4-methyl thiosemicarbazone: Synthesis, structural characterization and biological application. Polyhedron. 2013 Feb;50(1):264–9.
  • 17. Małecki JG, Maroń A, Serda M, Polański J. Ruthenium(II) carbonyl complexes with thiosemicarbazone ligands. Polyhedron. 2013 Jun;56:44–54.
  • 18. Eğlence S, Şahin M, Özyürek M, Apak R, Ülküseven B. Dioxomolybdenum(VI) complexes of S-methyl-5-bromosalicylidene-N-alkyl substituted thiosemicarbazones: Synthesis, catalase inhibition and antioxidant activities. Inorganica Chimica Acta. 2018 Jan;469:495–502.
  • 19. Güveli Ş. Nickel(II)-PPh 3 complexes of substituted benzophenone thiosemicarbazones: Electrochemistry, structural analysis, and antioxidant properties. Journal of Coordination Chemistry. 2020 Jan 2;73(1):137–53.
  • 20. Takjoo R, Hashemzadeh A, Rudbari HA, Nicolò F. Copper(II) and molybdenum(VI) complexes with 5-bromosalicylaldehyde S -allylisothiosemicarbazone: Syntheses, characterizations and crystal structures. Journal of Coordination Chemistry. 2013 Jan 1;66(2):345–57. 21. Yampolskaya M, Shova S, Gerbeleu N, Belskii V, Simonov YA. Synthesis And Structure Of [S-Methyl-N1, N4-Bıs (Salicylidene) Thiosemicarbazide] Ferrochloride (III). Zhurnal Neorganıcheskoı Khımıı. 1982;27(10):2551–7.
  • 22. Şahin M, Eğlence-Bakır S, Alpay M, Alpay S, Özmerdivenli R, Ülküseven B. Effective copper(II) and nickel(II) complexes with N3O and ON3 thiosemicarbazidato ligands. Synthesis, structural analysis and in vitro cytotoxity on melanoma B16F10 cells. Inorganica Chimica Acta. 2020 Mar;502:119347.
  • 23. Hille R. The Mononuclear Molybdenum Enzymes. Chem Rev. 1996 Jan 1;96(7):2757–816.
  • 24. Hussein MA, Guan TS, Haque RA, Ahamed MBK, Majid AMSA. Synthesis and characterization of thiosemicarbazonato molybdenum(VI) complexes: In vitro DNA binding, cleavage, and antitumor activities. Polyhedron. 2015 Jan;85:93–103.
  • 25. Duman S, Kızılcıklı İ, Koca A, Akkurt M, Ülküseven B. ONN-complexes of dioxomolybdenum(VI) with 2-hydroxy-1-naphthaldehyde S-ethyl-4-H/phenyl-thiosemicarbazones: Crystal structure, electrochemistry and in situ spectroelectrochemistry. Polyhedron. 2010 Oct;29(15):2924–32.
  • 26. Duman S, Kizilcikli İ, Ülküseven B. Dioxomolybdenum(VI) Complexes of 5-Bromo/3,5-Dibromo-Salicylaldehyde 4-(H/C 6 H 5 )- S -Propyl-Thiosemicarbazones. Phosphorus, Sulfur, and Silicon and the Related Elements. 2015 Mar 4;190(3):342–51.
  • 27. Moradi-Shoeili Z, Boghaei DM, Amini M, Bagherzadeh M, Notash B. New molybdenum(VI) complex with ONS-donor thiosemicarbazone ligand: Preparation, structural characterization, and catalytic applications in olefin epoxidation. Inorganic Chemistry Communications. 2013 Jan;27:26–30.
  • 28. Vrdoljak V, Đilović I, Cindrić M, Matković-Čalogović D, Strukan N, Gojmerac-Ivšić A, et al. Synthesis, structure and properties of eight novel molybdenum(VI) complexes of the types: [MoO2LD] and [{MoO2L}2D] (L=thiosemicarbazonato ligand, D=N-donor molecule). Polyhedron. 2009 Apr;28(5):959–65.
  • 29. Takjoo R, Akbari A, Ahmadi M, Amiri Rudbari H, Bruno G. Synthesis, spectroscopy, DFT and crystal structure investigations of 3-methoxy-2-hydroxybenzaldehyde S-ethylisothiosemicarbazone and its Ni(II) and Mo(VI) complexes. Polyhedron. 2013 May;55:225–32.<DOI>.
  • 30. Yamazaki C. The structure of isothiosemicarbazones. Canadian Journal of Chemistry. 1975;53(4):610–5.
  • 31. Anonymous. SHELXTL, software version 6.14. Bruker AXS Inc., Madison, WI; 2000.
  • 32. Farrugia LJ. ORTEP -3 for Windows - a version of ORTEP -III with a Graphical User Interface (GUI). J Appl Crystallogr. 1997 Oct 1;30(5):565–565.
  • 33. Eğlence-Bakır S, Şahin M, Zahoor M, Dilmen-Portakal E, Ülküseven B. Synthesis and biological potentials of dioxomolybdenum(VI) complexes with ONS and ONN chelating thiosemicarbazones: DNA-binding, antioxidant and enzyme inhibition studies. Polyhedron. 2020 Nov;190:114754.
  • 34. Kaya Y, Erçağ A, Kaya K. Synthesis, characterization and antioxidant activities of dioxomolybdenum(VI) complexes of new Schiff bases derived from substituted benzophenones. Journal of Coordination Chemistry. 2018 Oct 18;71(20):3364–80.
  • 35. Çelen Ş, Eğlence-Bakır S, Şahin M, Deniz I, Celik H, Kizilcikli I. Synthesis and characterization of new thiosemicarbazonato molybdenum(VI) complexes and their in vitro antimicrobial activities. Journal of Coordination Chemistry. 2019 May 19;72(10):1747–58.
  • 36. Plyler EK. Infrared spectra of methanol, ethanol, and n-propanol. J Res Natl Bur Stand. 1952;48(4):281–6.
  • 37. Vrdoljak V, Cindrić M, Milić D, Matković-Čalogović D, Novak P, Kamenar B. Synthesis of five new molybdenum(VI) thiosemicarbazonato complexes. Crystal structures of salicylaldehyde and 3-methoxy-salicylaldehyde 4-methylthiosemicarbazones and their molybdenum(VI) complexes. Polyhedron. 2005 Sep;24(13):1717–26.
  • 38. Novak P, Pičuljan K, Hrenar T, Smrečki V. Structure and Hydrogen Bonding Interactions in Methoxysalicylaldehyde Thiosemicarbazone Derivatives in Solution by NMR and DFT Methods. Croatica Chemica Acta. 2009;82(2):477–83.

Yıl 2021, Cilt 8, Sayı 4, 1275 - 1300, 30.11.2021
https://doi.org/10.18596/jotcsa.989318

Öz

Kaynakça

  • 1. Leovac V, Gerbeleu N, Canic V. Coordination compounds of cobalt (III), chromium (III), and vanadium (III) with salicylaldehyde S-methylthiosemicarbazone. Russ J Inorg Chem. 1982;27:514–7.
  • 2. Nehar OK, Mahboub R, Louhibi S, Roisnel T, Aissaoui M. New thiosemicarbazone Schiff base ligands: Synthesis, characterization, catecholase study and hemolytic activity. Journal of Molecular Structure. 2020 Mar;1204:127566.
  • 3. Behnisch R, Mietzsch F, Schmidt H. Chemical Studies on Thiosemicarbazones with Particular Reference to Antituberculous Acitivity. American review of tuberculosis. 1950;61(1):1–7.
  • 4. Plech T, Wujec M, Siwek A, Kosikowska U, Malm A. Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety. European Journal of Medicinal Chemistry. 2011 Jan;46(1):241–8.
  • 5. Kesel AJ. Broad-spectrum antiviral activity including human immunodeficiency and hepatitis C viruses mediated by a novel retinoid thiosemicarbazone derivative. European Journal of Medicinal Chemistry. 2011 May;46(5):1656–64.
  • 6. Li MX, Chen CL, Zhang D, Niu JY, Ji BS. Mn(II), Co(II) and Zn(II) complexes with heterocyclic substituted thiosemicarbazones: Synthesis, characterization, X-ray crystal structures and antitumor comparison. European Journal of Medicinal Chemistry. 2010 Jul;45(7):3169–77.
  • 7. Rodríguez-Argüelles MC, López-Silva EC, Sanmartín J, Pelagatti P, Zani F. Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: Inhibitory activity against fungi and bacteria. Journal of Inorganic Biochemistry. 2005 Nov;99(11):2231–9.
  • 8. Saswati, Dinda R, Schmiesing CS, Sinn E, Patil YP, Nethaji M, et al. Mixed-ligand nickel(II) thiosemicarbazone complexes: Synthesis, characterization and biological evaluation. Polyhedron. 2013 Feb;50(1):354–63.
  • 9. Viñuelas-Zahínos E, Luna-Giles F, Torres-García P, Fernández-Calderón MC. Co(III), Ni(II), Zn(II) and Cd(II) complexes with 2-acetyl-2-thiazoline thiosemicarbazone: Synthesis, characterization, X-ray structures and antibacterial activity. European Journal of Medicinal Chemistry. 2011 Jan;46(1):150–9.
  • 10. Chen J, Huang Y, Liu G, Afrasiabi Z, Sinn E, Padhye S, et al. The cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells. Toxicology and Applied Pharmacology. 2004 May;197(1):40–8.
  • 11. Afrasiabi Z. Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line, T47D. Journal of Inorganic Biochemistry. 2003 Jul 1;95(4):306–14.
  • 12. Eğlence-Bakır S, Sacan O, Şahin M, Yanardag R, Ülküseven B. Dioxomolybdenum(VI) complexes with 3-methoxy salicylidene-N-alkyl substituted thiosemicarbazones. Synthesis, characterization, enzyme inhibition and antioxidant activity. Journal of Molecular Structure. 2019 Oct;1194:35–41.
  • 13. Eğlence-Bakır S. New nickel(II) complexes containing N2O2 donor thiosemicarbazones: Synthesis, characterization and antioxidant properties. Journal of Molecular Structure. 2021 Dec;1246:131121.
  • 14. Bakkar MS, Siddiqi MY, Monshi MS. Preparation and Investegation of the Bonding Mode in the Complexes of Pt(II) with Thiosemicarbazone Ligands. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 2003 Jan 8;33(7):1157–69.
  • 15. Ren P, Liu T, Qin J, Chen C. Synthesis, Crystal Structure, Spectroscopy and Calculated First-Order Molecular Hyperpolarizability of a New Square-pyramidal Complex Zn(DMABT)(acac) 2. Journal of Coordination Chemistry. 2003 Jan 1;56(2):125–32.
  • 16. Sankaraperumal A, Karthikeyan J, Shetty AN, Lakshmisundaram R. Nickel(II) complex of p-[N,N-bis(2-chloroethyl)amino]benzaldehyde-4-methyl thiosemicarbazone: Synthesis, structural characterization and biological application. Polyhedron. 2013 Feb;50(1):264–9.
  • 17. Małecki JG, Maroń A, Serda M, Polański J. Ruthenium(II) carbonyl complexes with thiosemicarbazone ligands. Polyhedron. 2013 Jun;56:44–54.
  • 18. Eğlence S, Şahin M, Özyürek M, Apak R, Ülküseven B. Dioxomolybdenum(VI) complexes of S-methyl-5-bromosalicylidene-N-alkyl substituted thiosemicarbazones: Synthesis, catalase inhibition and antioxidant activities. Inorganica Chimica Acta. 2018 Jan;469:495–502.
  • 19. Güveli Ş. Nickel(II)-PPh 3 complexes of substituted benzophenone thiosemicarbazones: Electrochemistry, structural analysis, and antioxidant properties. Journal of Coordination Chemistry. 2020 Jan 2;73(1):137–53.
  • 20. Takjoo R, Hashemzadeh A, Rudbari HA, Nicolò F. Copper(II) and molybdenum(VI) complexes with 5-bromosalicylaldehyde S -allylisothiosemicarbazone: Syntheses, characterizations and crystal structures. Journal of Coordination Chemistry. 2013 Jan 1;66(2):345–57. 21. Yampolskaya M, Shova S, Gerbeleu N, Belskii V, Simonov YA. Synthesis And Structure Of [S-Methyl-N1, N4-Bıs (Salicylidene) Thiosemicarbazide] Ferrochloride (III). Zhurnal Neorganıcheskoı Khımıı. 1982;27(10):2551–7.
  • 22. Şahin M, Eğlence-Bakır S, Alpay M, Alpay S, Özmerdivenli R, Ülküseven B. Effective copper(II) and nickel(II) complexes with N3O and ON3 thiosemicarbazidato ligands. Synthesis, structural analysis and in vitro cytotoxity on melanoma B16F10 cells. Inorganica Chimica Acta. 2020 Mar;502:119347.
  • 23. Hille R. The Mononuclear Molybdenum Enzymes. Chem Rev. 1996 Jan 1;96(7):2757–816.
  • 24. Hussein MA, Guan TS, Haque RA, Ahamed MBK, Majid AMSA. Synthesis and characterization of thiosemicarbazonato molybdenum(VI) complexes: In vitro DNA binding, cleavage, and antitumor activities. Polyhedron. 2015 Jan;85:93–103.
  • 25. Duman S, Kızılcıklı İ, Koca A, Akkurt M, Ülküseven B. ONN-complexes of dioxomolybdenum(VI) with 2-hydroxy-1-naphthaldehyde S-ethyl-4-H/phenyl-thiosemicarbazones: Crystal structure, electrochemistry and in situ spectroelectrochemistry. Polyhedron. 2010 Oct;29(15):2924–32.
  • 26. Duman S, Kizilcikli İ, Ülküseven B. Dioxomolybdenum(VI) Complexes of 5-Bromo/3,5-Dibromo-Salicylaldehyde 4-(H/C 6 H 5 )- S -Propyl-Thiosemicarbazones. Phosphorus, Sulfur, and Silicon and the Related Elements. 2015 Mar 4;190(3):342–51.
  • 27. Moradi-Shoeili Z, Boghaei DM, Amini M, Bagherzadeh M, Notash B. New molybdenum(VI) complex with ONS-donor thiosemicarbazone ligand: Preparation, structural characterization, and catalytic applications in olefin epoxidation. Inorganic Chemistry Communications. 2013 Jan;27:26–30.
  • 28. Vrdoljak V, Đilović I, Cindrić M, Matković-Čalogović D, Strukan N, Gojmerac-Ivšić A, et al. Synthesis, structure and properties of eight novel molybdenum(VI) complexes of the types: [MoO2LD] and [{MoO2L}2D] (L=thiosemicarbazonato ligand, D=N-donor molecule). Polyhedron. 2009 Apr;28(5):959–65.
  • 29. Takjoo R, Akbari A, Ahmadi M, Amiri Rudbari H, Bruno G. Synthesis, spectroscopy, DFT and crystal structure investigations of 3-methoxy-2-hydroxybenzaldehyde S-ethylisothiosemicarbazone and its Ni(II) and Mo(VI) complexes. Polyhedron. 2013 May;55:225–32.<DOI>.
  • 30. Yamazaki C. The structure of isothiosemicarbazones. Canadian Journal of Chemistry. 1975;53(4):610–5.
  • 31. Anonymous. SHELXTL, software version 6.14. Bruker AXS Inc., Madison, WI; 2000.
  • 32. Farrugia LJ. ORTEP -3 for Windows - a version of ORTEP -III with a Graphical User Interface (GUI). J Appl Crystallogr. 1997 Oct 1;30(5):565–565.
  • 33. Eğlence-Bakır S, Şahin M, Zahoor M, Dilmen-Portakal E, Ülküseven B. Synthesis and biological potentials of dioxomolybdenum(VI) complexes with ONS and ONN chelating thiosemicarbazones: DNA-binding, antioxidant and enzyme inhibition studies. Polyhedron. 2020 Nov;190:114754.
  • 34. Kaya Y, Erçağ A, Kaya K. Synthesis, characterization and antioxidant activities of dioxomolybdenum(VI) complexes of new Schiff bases derived from substituted benzophenones. Journal of Coordination Chemistry. 2018 Oct 18;71(20):3364–80.
  • 35. Çelen Ş, Eğlence-Bakır S, Şahin M, Deniz I, Celik H, Kizilcikli I. Synthesis and characterization of new thiosemicarbazonato molybdenum(VI) complexes and their in vitro antimicrobial activities. Journal of Coordination Chemistry. 2019 May 19;72(10):1747–58.
  • 36. Plyler EK. Infrared spectra of methanol, ethanol, and n-propanol. J Res Natl Bur Stand. 1952;48(4):281–6.
  • 37. Vrdoljak V, Cindrić M, Milić D, Matković-Čalogović D, Novak P, Kamenar B. Synthesis of five new molybdenum(VI) thiosemicarbazonato complexes. Crystal structures of salicylaldehyde and 3-methoxy-salicylaldehyde 4-methylthiosemicarbazones and their molybdenum(VI) complexes. Polyhedron. 2005 Sep;24(13):1717–26.
  • 38. Novak P, Pičuljan K, Hrenar T, Smrečki V. Structure and Hydrogen Bonding Interactions in Methoxysalicylaldehyde Thiosemicarbazone Derivatives in Solution by NMR and DFT Methods. Croatica Chemica Acta. 2009;82(2):477–83.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya, İnorganik ve Nükleer
Bölüm Makaleler
Yazarlar

Songül EĞLENCE BAKIR (Sorumlu Yazar)
Istanbul University
0000-0001-6121-0333
Türkiye

Yayımlanma Tarihi 30 Kasım 2021
Başvuru Tarihi 1 Eylül 2021
Kabul Tarihi 10 Kasım 2021
Yayınlandığı Sayı Yıl 2021, Cilt 8, Sayı 4

Kaynak Göster

Vancouver Eğlence Bakır S. Dioxomolybdenum(VI) complexes of ONN chelating thiosemicarbazones: Crystallographic and spectroscopic (UV, IR and NMR) studies. Journal of the Turkish Chemical Society Section A: Chemistry. 2021; 8(4): 1275-1300.
J. Turk. Chem. Soc., Sect. A: Chem.