Abstract
Metalosen içerikli bilinen bir ferrosenilditiyofosfonato Ni(II) kompleksinin [Ni(FcL)2], (FcL= O-1-fenil-1-propil (ferrosenil)ditiyofosfonat), bis(difenilfosfino)metan (DPPM) ve Na[B(Ph)4] ile reaksiyonundan yeni bis-(difenilfosfino)metan[O-1-fenil-1-propil(ferrosenil)ditiyofosfonato]Ni(II)tetrafenilborat ([Ni(FcL)(DPPM)]+[BPh4]-), iyonik kompleksi sentezlendi. Kompleksin yapısı element analizi, titreşim spektroskopisi (FT-IR ve Raman), MS (MALDI-TOF) ve 31P- NMR yöntemleriyle karakterize edildi. 31P-NMR analizi, spektrumdaki fosfor atomunun alan integrallerinin molekülde üç fosfor atomu olduğunu doğrulamaktadır.
Keywords
Fosfonoditiyoato Ni(II) kompleksleri Tetrafenilborat Fosfin Ligandları Ferrosenil Ditiyofosfonik Asitler
Supporting Institution
TÜBİTAK, 2209-A Üniversite Öğrencileri Araştırma Projeleri Destekleme Programı
Project Number
TÜBİTAK 2209-A
Thanks
Yazarlar bu çalışmaya “Üniversite Öğrencileri Araştırma Projeleri Destekleme Programı” kapsamında finansal destekte bulunan “TÜBİTAK 2209-A” projesine teşekkür ederler.
References
- 1. Van-Zyl WE. Dithiophosphonates And Related P/S-Type Ligands of Group 11 Metals. Com Inorg Chem. 2010; 31: 13-45.
- 2. Fay P, Lankelma HP. The Reaction of Cyclohexene with Phosphorus Pentasulfide. J Am Chem Soc. 1952; 74: 4933-4935.
- 3. Contarini S, Tripaldi G, Ponti G, et al. Surface investigation of lubricant–metal interactions by synchrotron photoemission spectroscopy. App Surf Sci. 1997; 108: 359-364.
- 4. Fuller M, Yin Z, Kasrai M, et al. Chemical characterization of tribochemical and thermal films generated from neutral and basic ZDDPs using X-ray absorption spectroscopy. Tribol Int. 1997; 30: 305-315.
- 5. Cava MP, Levınson MI. Thıonation Reactions Of Lawesson’s Reagents. Tetrahedron. 1985; 41: 5061-5087.
- 6. Newallis PE, Chupp JP, Groenweghe LCD. Thionophosphine Sulfides. I. Preparation and Use in the Friedel-Crafts Reaction. J Org Chem. 1962; 27: 3829-3831.
- 7. Sağlam EG, Bulat E, Yılmaz H. The Syntheses and Characterization of New Dithiophosphonates derived from Novel 2,4-Bis(methoxytolyl)-1,3-dithia-2,4-diphosphetane 2,4- disulfides and Their Ni(II) Complexes. JOTCSA. 2020; 7: 789-800.
- 8. Bulat E, Sağlam EG, Zeyrek CT, et al. Ni(II) complexes with 1,3,2,4-dithiadiphosphetane 2,4-disulfide-based ligands: Structural insights, theoretical studies, and anticancer activities. Appl Organomet Chem. 2022; 36: e6821.
- 9. Bulat E, Sağlam EG, Zeyrek CT, et al. 2,4-Bis(2,4-dimethoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide and its derivatives: Syntheses, structural characterizations, anticancer activities, and theoretical studies on some dithiophosphonato Ni(II) complex. J Mol Struct. 2023; 1272: 134197.
- 10. Van Zyl WE, Facler JP. A General and Convenient Route to Dithiophosphonate Salt Derivatives. Phosphorus, Sulfur, Silicon Relat Elem. 2000; 167: 117-132.
- 11. Foreman MStJ, Slawin AMZ, Woollins JD. 2, 4-Diferrocenyl-1,3-dithiadiphosphetane 2,4-disulfide; structure and reactions with catechols and [PtCl2(PR3)2] (R= Et or Bun). J Chem Soc Dalton Trans. 1996; 18: 3653-3657.
- 12. Sağlam EG, Akkoç S, Zorlu Y, et al. New phenanthroline nickel(II) organodithio-phosphorus complexes: Syntheses, structural characterizations and in vitro cytotoxic activity studies. Polyhedron. 2021; 199: 1-13.
- 13. Sağlam EG, Erden S, Tutsak Ö, et al. Syntheses, characterization of and studies on the electrochemical behaviour of ferrocenyl dithiophosphonates and 4-methoxyphenyl dithiophosphonates. Phosphorus, Sulfur, Silicon Relat Elem. 2017: 192; 322-329.
- 14. Karakus M, Lonnecke P, Yakhvarov D, et al. Heterobimetallic Nickel(II)Complexes of Ferrocenyldithiophosphonates. Molecular Structures of [{FcP(OR)S2}2Ni] [Fc Fe(η5 -C5H4)(η5-C5H5), R= Et, Pri , Bus , Bui ]. Z Anorg Allg Chem. 2004; 630: 1444-1450.
- 15. Sağlam EG, Akkoç S, Zeyrek CT, et al. New heterobimetallic nickel(II) ferrocenyldithiophosphonato complexes: Syntheses, characterization, antiproliferative activity and X-ray, DFT, molecular docking studies on trans-bis- [O-3-methyl- 1-butyl- (ferrocenyl) dithiophosphonato] nickel(II). Inorg Chim Acta. 2021; 514: 119991.
- 16. Sağlam EG, Akkoç S, Acar N, et al. New Heterobimetallic Ferrocenyl Dithiophosphonato Cd(II) and Hg(II) Complexes: DNA Interactions, Antimicrobial and Anticancer Activity Studies of the Cd(II) Complexes. ChemistrySelect. 2021; 6: 12496-12505.
- 17. Gray IP, Milton HL, Slawin AMZ, et al. Synthesis and structure of [Fc(RO)PS2] complexes. Dalton Trans. 2003; 17: 3450-3457.
- 18. Sağlam EG., Çelik Ö, Yılmaz H, et al., Synthesis, spectroscopic characterization and X-ray single crystal structures of trans-bis[4-methoxyphenyl (3-methylbutyl) dithiophosphinato] nickel(II) and bis [4-methoxyphenyl (3-methylbutyl) dithiophosphinato] cobalt(II) complexes. Trans Met Chem. 2010; 35: 399-405.
- 19. Esterhuysen C, Kruger GJ, Blewett G, et al., 4-Membered metallodithiophosphinate rings - flat or puckered? A comparison of two crystal structures with computational and literature data. Inorg Chim Acta. 2006; 359: 609-616.
- 20. Duffy ST, Nicholson BK, Henderson W. Di-isobutyldithiophosphinate complexes of nickel(II), palladium(II) and platinum(II) with ancillary phosphine ligands. J Sulfur Chem. 2011; 32: 443-450.
- 21. Ferraro JR, Wang JT, Udovich C, et al. Low-frequency infrared spectra of planar and tetrahedral nickel bromide complexes of diphenylalkylphosphines. Inorg Chem. 1970; 9:12, 2675-2678.
- 22. Exarchos G, Robinson SD, Steed JW. The synthesis of new bimetallic complex salts by halide/sulfur chelate cross transfer: X-ray crystal structures of the salts [Ni(S2CNEt2)(dppe)]2[HgBr4], [Pt(S2CNEt2) (dppe)]2 [CdCl4], [Co(S2CNEt2)2(dppe)]2 [Cl3ZnO: (Ph)2PCH2CH2P(Ph)2: OZnCl3] and [Pd(S2CNnBu2)(bipy)]2[CdCl4]. Polyhedron. 2001; 20: 2951-2963.
- 23. Karakus M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russ J Coord Chem. 2006; 32: 437-443.
- 24. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org Mass Spectrom. 1984: 19; 82-86.
- 25. Sağlam EG, Ebinç A, Zeyrek CT, et al., Structural studies on some dithiophosphonato complexes of Ni(II), Cd(II), Hg(II) and theoretical studies on a dithiophosphonato Ni(II) complex using density functional theory. J Mol Struct. 2015: 1099; 490-501.
- 26. Chakravarty M, Pailloux S, Ouizem S, et al., Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl)phosphinodithioic acid, [2-C5H4N]CH2P(S)(SH)(Ph). Polyhedron. 2012: 33; 327-335.
Synthesis and Structural Investigation of a New Phosphino Metallocene Dithiophosphonato Nickel Complex
Abstract
A new bis-(diphenylphosphino) methan [O-1-phenyl-1-propyl (ferrocenyl) dithiophosphonate] Ni(II) tetraphenylborat ([Ni(FcL)(DPPM)]+[BPh4]-; FcL= O-1-phenyl-1-propyl(ferrocenyl)dithiophosphonates, DPPM= bis(diphenylphosphino)methane ), ionic complex was synthesized from the reaction of ferrocenyldithiophosphonato Ni(II) complex containing metallocene [Ni(FcL)2] which is known with DPPM and Na[B(Ph)4]. The structure of the synthesized complex was characterized by elemental analysis, vibrational spectroscopy (FT-IR and Raman), MS (MALDI-TOF) and 31P-NMR methods. Spectroscopic methods confirm the suggested structure. 31P-NMR analysis confirms that the field integrals of the phosphorus atom in the spectrum have three phosphorus atoms in the molecule.
Keywords
Ferrocenyl Dithiophosphonic acids Phosphonodithioato Ni(II) complexes Tetraphenylborate Phosphine ligands
Project Number
TÜBİTAK 2209-A
References
- 1. Van-Zyl WE. Dithiophosphonates And Related P/S-Type Ligands of Group 11 Metals. Com Inorg Chem. 2010; 31: 13-45.
- 2. Fay P, Lankelma HP. The Reaction of Cyclohexene with Phosphorus Pentasulfide. J Am Chem Soc. 1952; 74: 4933-4935.
- 3. Contarini S, Tripaldi G, Ponti G, et al. Surface investigation of lubricant–metal interactions by synchrotron photoemission spectroscopy. App Surf Sci. 1997; 108: 359-364.
- 4. Fuller M, Yin Z, Kasrai M, et al. Chemical characterization of tribochemical and thermal films generated from neutral and basic ZDDPs using X-ray absorption spectroscopy. Tribol Int. 1997; 30: 305-315.
- 5. Cava MP, Levınson MI. Thıonation Reactions Of Lawesson’s Reagents. Tetrahedron. 1985; 41: 5061-5087.
- 6. Newallis PE, Chupp JP, Groenweghe LCD. Thionophosphine Sulfides. I. Preparation and Use in the Friedel-Crafts Reaction. J Org Chem. 1962; 27: 3829-3831.
- 7. Sağlam EG, Bulat E, Yılmaz H. The Syntheses and Characterization of New Dithiophosphonates derived from Novel 2,4-Bis(methoxytolyl)-1,3-dithia-2,4-diphosphetane 2,4- disulfides and Their Ni(II) Complexes. JOTCSA. 2020; 7: 789-800.
- 8. Bulat E, Sağlam EG, Zeyrek CT, et al. Ni(II) complexes with 1,3,2,4-dithiadiphosphetane 2,4-disulfide-based ligands: Structural insights, theoretical studies, and anticancer activities. Appl Organomet Chem. 2022; 36: e6821.
- 9. Bulat E, Sağlam EG, Zeyrek CT, et al. 2,4-Bis(2,4-dimethoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide and its derivatives: Syntheses, structural characterizations, anticancer activities, and theoretical studies on some dithiophosphonato Ni(II) complex. J Mol Struct. 2023; 1272: 134197.
- 10. Van Zyl WE, Facler JP. A General and Convenient Route to Dithiophosphonate Salt Derivatives. Phosphorus, Sulfur, Silicon Relat Elem. 2000; 167: 117-132.
- 11. Foreman MStJ, Slawin AMZ, Woollins JD. 2, 4-Diferrocenyl-1,3-dithiadiphosphetane 2,4-disulfide; structure and reactions with catechols and [PtCl2(PR3)2] (R= Et or Bun). J Chem Soc Dalton Trans. 1996; 18: 3653-3657.
- 12. Sağlam EG, Akkoç S, Zorlu Y, et al. New phenanthroline nickel(II) organodithio-phosphorus complexes: Syntheses, structural characterizations and in vitro cytotoxic activity studies. Polyhedron. 2021; 199: 1-13.
- 13. Sağlam EG, Erden S, Tutsak Ö, et al. Syntheses, characterization of and studies on the electrochemical behaviour of ferrocenyl dithiophosphonates and 4-methoxyphenyl dithiophosphonates. Phosphorus, Sulfur, Silicon Relat Elem. 2017: 192; 322-329.
- 14. Karakus M, Lonnecke P, Yakhvarov D, et al. Heterobimetallic Nickel(II)Complexes of Ferrocenyldithiophosphonates. Molecular Structures of [{FcP(OR)S2}2Ni] [Fc Fe(η5 -C5H4)(η5-C5H5), R= Et, Pri , Bus , Bui ]. Z Anorg Allg Chem. 2004; 630: 1444-1450.
- 15. Sağlam EG, Akkoç S, Zeyrek CT, et al. New heterobimetallic nickel(II) ferrocenyldithiophosphonato complexes: Syntheses, characterization, antiproliferative activity and X-ray, DFT, molecular docking studies on trans-bis- [O-3-methyl- 1-butyl- (ferrocenyl) dithiophosphonato] nickel(II). Inorg Chim Acta. 2021; 514: 119991.
- 16. Sağlam EG, Akkoç S, Acar N, et al. New Heterobimetallic Ferrocenyl Dithiophosphonato Cd(II) and Hg(II) Complexes: DNA Interactions, Antimicrobial and Anticancer Activity Studies of the Cd(II) Complexes. ChemistrySelect. 2021; 6: 12496-12505.
- 17. Gray IP, Milton HL, Slawin AMZ, et al. Synthesis and structure of [Fc(RO)PS2] complexes. Dalton Trans. 2003; 17: 3450-3457.
- 18. Sağlam EG., Çelik Ö, Yılmaz H, et al., Synthesis, spectroscopic characterization and X-ray single crystal structures of trans-bis[4-methoxyphenyl (3-methylbutyl) dithiophosphinato] nickel(II) and bis [4-methoxyphenyl (3-methylbutyl) dithiophosphinato] cobalt(II) complexes. Trans Met Chem. 2010; 35: 399-405.
- 19. Esterhuysen C, Kruger GJ, Blewett G, et al., 4-Membered metallodithiophosphinate rings - flat or puckered? A comparison of two crystal structures with computational and literature data. Inorg Chim Acta. 2006; 359: 609-616.
- 20. Duffy ST, Nicholson BK, Henderson W. Di-isobutyldithiophosphinate complexes of nickel(II), palladium(II) and platinum(II) with ancillary phosphine ligands. J Sulfur Chem. 2011; 32: 443-450.
- 21. Ferraro JR, Wang JT, Udovich C, et al. Low-frequency infrared spectra of planar and tetrahedral nickel bromide complexes of diphenylalkylphosphines. Inorg Chem. 1970; 9:12, 2675-2678.
- 22. Exarchos G, Robinson SD, Steed JW. The synthesis of new bimetallic complex salts by halide/sulfur chelate cross transfer: X-ray crystal structures of the salts [Ni(S2CNEt2)(dppe)]2[HgBr4], [Pt(S2CNEt2) (dppe)]2 [CdCl4], [Co(S2CNEt2)2(dppe)]2 [Cl3ZnO: (Ph)2PCH2CH2P(Ph)2: OZnCl3] and [Pd(S2CNnBu2)(bipy)]2[CdCl4]. Polyhedron. 2001; 20: 2951-2963.
- 23. Karakus M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russ J Coord Chem. 2006; 32: 437-443.
- 24. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org Mass Spectrom. 1984: 19; 82-86.
- 25. Sağlam EG, Ebinç A, Zeyrek CT, et al., Structural studies on some dithiophosphonato complexes of Ni(II), Cd(II), Hg(II) and theoretical studies on a dithiophosphonato Ni(II) complex using density functional theory. J Mol Struct. 2015: 1099; 490-501.
- 26. Chakravarty M, Pailloux S, Ouizem S, et al., Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl)phosphinodithioic acid, [2-C5H4N]CH2P(S)(SH)(Ph). Polyhedron. 2012: 33; 327-335.
Details
| Primary Language | Turkish |
|---|---|
| Subjects | Transition Metal Chemistry |
| Journal Section | Research Articles |
| Authors | |
| Project Number | TÜBİTAK 2209-A |
| Publication Date | May 21, 2025 |
| Submission Date | March 7, 2024 |
| Acceptance Date | June 24, 2024 |
| Published in Issue | Year 2025 Volume: 5 Issue: 1 |
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