New Homodinuclear Alkyl and Aryl Dithiophosphonato Cd(II) and Hg(II) complexes: Syntheses and Characterizations
Year 2020,
, 49 - 64, 15.02.2020
Ertuğrul Gazi Sağlam
,
Elif Bulat
,
Nurcan Acar
,
İbrahim Demirel
Abstract
New Cd(II) and Hg(II) complexes of previously
known five dithiophosphonic acids ((p-MeO-C6H4)PS(SH)(OR), HLn, (n=
1-5); R= 3-pentyl-, HL1; R=1-phenyl-1-propyl-,
HL2; R= 4-tert-butyl benzyl-,
HL3; R= diphenylmethyl-, HL4;
R= 4-tert- butyl cyclohexyl-, HL5) were
prepared and characterized. To do this, the dithiophosphonic
acids involved were treated with stoichiometric amount of the corresponding
metal salts in methyl alcohol. The complexes came of as powdery crystals and were
recrystallized from chloroform. The pure complexes were characterized by using
elemental analyses as well as mas-(ESI), FTIR-, Raman-, NMR- (1H, 13C, 31P) spectroscopies.
Supporting Institution
Project Coordination Application and Research Center of Bozok University
Project Number
BAP 6602b-FEN/18-221
Thanks
This study is supported by the Project Coordination Application and Research Center of Bozok University [BAP 6602b-FEN/18-221].
References
- 1. Haiduc I. 1,1-Dithiolato Ligands in Comprehensive Coordination Chemistry II Edited by McCleverty JA, Meyer TJ. 2004; 1: 349-76.
- 2. Thomsen I, Clausen K, Scheibye S, Lawesson S-O. Thiation with 2,4-bis(4-Methoxyphenyl)-1,3,2,4- Dithiadiphosphetane 2,4-disulfide: N-methylthiopyrrolidone. Organic Syntheses, Coll. 1990; 7: 372.
- 3. Ozturk T, Ertas E, Mert O. A Berzelius Reagent, Phosphorus Decasulfide (P4S10), in Organic Syntheses, Chem. Rev. 2010; 110(6): 3419–78.
- 4. Kour M, Kumar S, Andotra S, Kour G, Singh G, Gupta VK, Rajni Kant R, Katoch M, Pandey S K. Chromium(III) complexes of dimethyl diphenyl dithiophosphates: Synthesis, characterization, and antibacterial studies. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192(10): 1–5.
- 5. Diemert K, Kuchen W. Synthesis of Dithiophosphinic Acids by Nucleophilic Fission of Perthiophosphonic Anhydrides. Angew. Chem. Internat. Edit. 1971; 10(7): 508–9.
- 6. Aydemir C, Solak S, Acar Doğanlı G, Şensoy T, Arar D, Bozbeyoglu Mercan Dogan N, Lönnecke P, Hey-Hawkins E, Şekerci M, Karakuş M, Synthesis, Characterization, and Antibacterial Activity of Dithiophosphonates and Amidodithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190(3): 300–9.
- 7. Karakuş M, Lönnecke P, Hey-Hawkins E. Zwitterionic ferrocenyl dithiophosphonates: the molecular structure of [FcP(S)S(OCH2CH2NH2Me)] [Fc=Fe(η5-C5H4)( η5-C5H5)]. Polyhedron, 2004; 23: 2281–84.
- 8. Van Zyl W E, Woollins J D. The coordination chemistry of dithiophosphonates: An emerging and versatile ligand class. Coord. Chem. Rev. 2013; 257: 718–73.
- 9. Haiduc I, Bryan Sowerby D. Stereochemical Aspects of Phosphor-1,1-Dithiolato Metal Complexes: Coordination Patterns, Molecular Structures and Supramolecular Associations in Dithiophosphinates and Related Compounds. Polyhedron 1995; 15(15): 2469-21.
- 10. Liu H-L, Mao H-Y, Chen X, Zhang H-Y, Hou H-W, Wu Q, Zhu Y, Ye B-X, Yuan L-J. Four novel sulfur-rich complexes: Syntheses, crystal structures of three nickel(II) and one cobalt(II) complex with derivatives of Lawesson’s Reagent. Polyhedron. 2004; 23: 1799–4.
- 11. Van Zyl W.E. Dithiophosphonates and Related P/S-Type Ligands of Group 11 Metals: Comments Inorg. Chem. 2010; 31(1-2): 13-45.
- 12. Gray I P, Milton H L, Slawin A M Z, Woollıns J. D. Synthesis and structure of [Fc(RO)PS2]- complexes. Dalton Trans. 2003; 3450–57.
- 13. Karakuş M, Yılmaz H, Bulak E, Lonnecke, P. Bis{µ-[O-cyclopentyl(4-methoxyphenyl) dithiophosphonato]1κ: S,2κ: S-[O-cyclopentyl (4- methoxyphenyl) dithiophosphonato] 1κ2S,S } dizinc (II). Appl. Organometal. Chem. 2005; 19: 396-97.
- 14. Harrison PG, Begley MJ, Kikabhai T, Killer F. Zinc(II) Bis(O,O'-dialkyl dithiophosphates): Interaction with Small Nitrogen Bases. The Crystal and Molecular Structure of Hexakis(µ-O,O'-diethyl dithiophosphate)-µ-thio-tetra zinc, Zn4[S2P(OEt)2]6S. Dalton Trans. 1986; 925– 28.
- 15. Guoxin T, Yongjun Z, Jingming X. Extraction of Am(III) and Ln(III) By Dialkyldithiophosphinic Acid with Different Alkyl Groups. Solvent Extr. Ion Exch. 2001; 19(6): 993–1005.
- 16. Yagishita K, Konishi S. Lubricating oil additive and lubricating oil composition. 2013; US 8,481,467.
- 17. Ziyatdinova GK, Budnikov GK, Samigullin AI, G Gabdullina T, Sofronov AV, Al’metkina LA, Nizamov IS, Cherkasov RA. Electrochemical Determination of Synthetic Antioxidants of Bisdithiophosphonic Acids. J. Anal. Chem. 2010; 65: 1273-79.
- 18. Cristau P, Dahmen P. Active compound combinations comprising carboxamide derivatives. 2017; US 9,801,374.
- 19. Bellande E, Comazzi V, Laine J, Lecayon M, Pasqualini R, Duatti A, Hoffschir D. Synthesis and Biodistribution of Nitrido Technetium-99m Radiopharmaceuticals with Dithiophosphinate Ligands: a Class of Brain Imaging Agents Nucl. Med. and Biol. 1995; 22(3): 315-20.
- 20. Pasqualini R, Bellande E, Comazzi V, Laine J. Radiopharmaceutical product having in particular a cerebral tropism comprising a nitro complex of a transition metal and method for preparing said product. 1996; US 5,496,929.
- 21. Pasqualini R, Comazzi V, Bellande E. Process for the preparation of nitride complexes of transition metals. 1995; US 5,399,339.
- 22. Feng W, Teo X-Y, Novera W, Ramanujulu PM, Lian D, Huan D, Moore PK, Deng L-W, Dymock BW. Discovery of New H2S Releasing Phosphordithioates and 2,3-Dihydro-2-phenyl-2-sulfanylenebenzo[d][1,3,2]oxazaphospholes with Improved Antiproliferative Activity. J. Med. Chem. 2015; 58(16): 6456–80.
- 23. Banaei A, Saadat A, McArdle P, Mohammad Goli M, Crystal structure, antibacterial activity and nanoparticles of Cd(II) complex derived from dithiophosphonate ligand. Phosphorus, Sulfur Silicon Relat. Elem. 2018; 193(6): 369-74.
- 24. Sağlam EG, Bulat E, Zeyrek CT, Dal H, Hökelek T. Syntheses of and structural studies on some square planar dithiophosphonato Ni(II) complexes, octahedral pyridine derivatives thereof and X-ray crystallography, DFT and molecular docking studies of the latter. J. Mol. Struc. 2019; 1178: 112–25.
- 25. Casas JS, García-Tasende MS, Sánchez A, Sordo J, Castellano EE, Zukerman-Schpector J. Synthesis, crystal structure and spectroscopic properties of bis(diphenyldithiophosphinato)cadmium(II). Inorg. Chim. Acta. 1994; 219(1–2): 115-19.
- 26. Shi W, Shafaei-Fallah M, Anson CE, Rothenberger A. Metal thiophosphonates and related compounds: an emerging area of supramolecular coordination chemistry. Dalton Trans. 2006; 26: 3257-62.
- 27. Czernuszewicz R, Maslowsky, E Jr, Nakamoto K. Infrared and Raman Spectra of Bis(imidotetraphenyldithiodiphosphino-S,S’) Complexes with Cu(II), Co(II) and Fe(II). Inorg. Chim. Acta. 1980; 40: 199-2.
- 28. Paddy JL, Lee NCJ, Waters DN, Trott W. Zinc Dialkyldithiophosphate Oxidation by Cumene Hydroperoxide: Kinetic Studies by Raman and 31P NMR Spectroscopy. J. Tribology Trans. 1990; 33(1): 15-20.
- 29. Larsson ML, Holmgren A. Reversible phase transition in Zn2(O,O-di(cyclohexyl)dithiophosphate)4, studied by Raman spectroscopy and compared with NMR results. Vib. Spectro. 2004; 34(2): 243-46.
- 30. Chakravarty M, Pailloux S, Ouizem S, Smith KA, Duesler EN, Paine RT, Williams NJ, Hancock RD. Synthesis and metal coordination chemistry of (phenyl)(pyridine-2-ylmethyl)phosphinodithioic acid. Polyhedron [2-C5H4N]CH2P(S)(SH)(Ph). 2012; 33: 327-35.
- 31. Karakuş M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russ. J. Coord Chem 2006; 32(6): 437–43.
- 32. Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von
Dithiophosphinsären. Phosphorus, Sulfur Silicon Relat. Elem. 1983; 14: 225-28.
- 33. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org. Mass Spectrom. 1984; 19: 82-86.
- 34. Karakuş M, Yılmaz H, Özcan Y, S İde. Appl. Crystallographic report: Bis{µ-[O-cyclopentyl (4-methoxyphenyl) dithiophosphonato] 1κ:S,2κ: S-[O-cyclopentyl(4-methoxyphenyl) dithiophosphonato]-1κ2S,S′}dicadmium(II). Organometal. Chem. 2004; 18: 141-42.
- 35. Ramirez RG, Toscano RA, Silverstru C, Haiduc I. Studies on inorganic tin diphenyldithiophosphinates. Crystal and molecular structure of CIS- dichlorobis(diphenyldithiophosphinato)tin(IV). Polyhedron 1996; 15(21): 3857–67.
- 36. Przychodzen W. New Products of Reaction of Lawesson's Reagent With Diols. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 1621–33.
Year 2020,
, 49 - 64, 15.02.2020
Ertuğrul Gazi Sağlam
,
Elif Bulat
,
Nurcan Acar
,
İbrahim Demirel
Project Number
BAP 6602b-FEN/18-221
References
- 1. Haiduc I. 1,1-Dithiolato Ligands in Comprehensive Coordination Chemistry II Edited by McCleverty JA, Meyer TJ. 2004; 1: 349-76.
- 2. Thomsen I, Clausen K, Scheibye S, Lawesson S-O. Thiation with 2,4-bis(4-Methoxyphenyl)-1,3,2,4- Dithiadiphosphetane 2,4-disulfide: N-methylthiopyrrolidone. Organic Syntheses, Coll. 1990; 7: 372.
- 3. Ozturk T, Ertas E, Mert O. A Berzelius Reagent, Phosphorus Decasulfide (P4S10), in Organic Syntheses, Chem. Rev. 2010; 110(6): 3419–78.
- 4. Kour M, Kumar S, Andotra S, Kour G, Singh G, Gupta VK, Rajni Kant R, Katoch M, Pandey S K. Chromium(III) complexes of dimethyl diphenyl dithiophosphates: Synthesis, characterization, and antibacterial studies. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192(10): 1–5.
- 5. Diemert K, Kuchen W. Synthesis of Dithiophosphinic Acids by Nucleophilic Fission of Perthiophosphonic Anhydrides. Angew. Chem. Internat. Edit. 1971; 10(7): 508–9.
- 6. Aydemir C, Solak S, Acar Doğanlı G, Şensoy T, Arar D, Bozbeyoglu Mercan Dogan N, Lönnecke P, Hey-Hawkins E, Şekerci M, Karakuş M, Synthesis, Characterization, and Antibacterial Activity of Dithiophosphonates and Amidodithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190(3): 300–9.
- 7. Karakuş M, Lönnecke P, Hey-Hawkins E. Zwitterionic ferrocenyl dithiophosphonates: the molecular structure of [FcP(S)S(OCH2CH2NH2Me)] [Fc=Fe(η5-C5H4)( η5-C5H5)]. Polyhedron, 2004; 23: 2281–84.
- 8. Van Zyl W E, Woollins J D. The coordination chemistry of dithiophosphonates: An emerging and versatile ligand class. Coord. Chem. Rev. 2013; 257: 718–73.
- 9. Haiduc I, Bryan Sowerby D. Stereochemical Aspects of Phosphor-1,1-Dithiolato Metal Complexes: Coordination Patterns, Molecular Structures and Supramolecular Associations in Dithiophosphinates and Related Compounds. Polyhedron 1995; 15(15): 2469-21.
- 10. Liu H-L, Mao H-Y, Chen X, Zhang H-Y, Hou H-W, Wu Q, Zhu Y, Ye B-X, Yuan L-J. Four novel sulfur-rich complexes: Syntheses, crystal structures of three nickel(II) and one cobalt(II) complex with derivatives of Lawesson’s Reagent. Polyhedron. 2004; 23: 1799–4.
- 11. Van Zyl W.E. Dithiophosphonates and Related P/S-Type Ligands of Group 11 Metals: Comments Inorg. Chem. 2010; 31(1-2): 13-45.
- 12. Gray I P, Milton H L, Slawin A M Z, Woollıns J. D. Synthesis and structure of [Fc(RO)PS2]- complexes. Dalton Trans. 2003; 3450–57.
- 13. Karakuş M, Yılmaz H, Bulak E, Lonnecke, P. Bis{µ-[O-cyclopentyl(4-methoxyphenyl) dithiophosphonato]1κ: S,2κ: S-[O-cyclopentyl (4- methoxyphenyl) dithiophosphonato] 1κ2S,S } dizinc (II). Appl. Organometal. Chem. 2005; 19: 396-97.
- 14. Harrison PG, Begley MJ, Kikabhai T, Killer F. Zinc(II) Bis(O,O'-dialkyl dithiophosphates): Interaction with Small Nitrogen Bases. The Crystal and Molecular Structure of Hexakis(µ-O,O'-diethyl dithiophosphate)-µ-thio-tetra zinc, Zn4[S2P(OEt)2]6S. Dalton Trans. 1986; 925– 28.
- 15. Guoxin T, Yongjun Z, Jingming X. Extraction of Am(III) and Ln(III) By Dialkyldithiophosphinic Acid with Different Alkyl Groups. Solvent Extr. Ion Exch. 2001; 19(6): 993–1005.
- 16. Yagishita K, Konishi S. Lubricating oil additive and lubricating oil composition. 2013; US 8,481,467.
- 17. Ziyatdinova GK, Budnikov GK, Samigullin AI, G Gabdullina T, Sofronov AV, Al’metkina LA, Nizamov IS, Cherkasov RA. Electrochemical Determination of Synthetic Antioxidants of Bisdithiophosphonic Acids. J. Anal. Chem. 2010; 65: 1273-79.
- 18. Cristau P, Dahmen P. Active compound combinations comprising carboxamide derivatives. 2017; US 9,801,374.
- 19. Bellande E, Comazzi V, Laine J, Lecayon M, Pasqualini R, Duatti A, Hoffschir D. Synthesis and Biodistribution of Nitrido Technetium-99m Radiopharmaceuticals with Dithiophosphinate Ligands: a Class of Brain Imaging Agents Nucl. Med. and Biol. 1995; 22(3): 315-20.
- 20. Pasqualini R, Bellande E, Comazzi V, Laine J. Radiopharmaceutical product having in particular a cerebral tropism comprising a nitro complex of a transition metal and method for preparing said product. 1996; US 5,496,929.
- 21. Pasqualini R, Comazzi V, Bellande E. Process for the preparation of nitride complexes of transition metals. 1995; US 5,399,339.
- 22. Feng W, Teo X-Y, Novera W, Ramanujulu PM, Lian D, Huan D, Moore PK, Deng L-W, Dymock BW. Discovery of New H2S Releasing Phosphordithioates and 2,3-Dihydro-2-phenyl-2-sulfanylenebenzo[d][1,3,2]oxazaphospholes with Improved Antiproliferative Activity. J. Med. Chem. 2015; 58(16): 6456–80.
- 23. Banaei A, Saadat A, McArdle P, Mohammad Goli M, Crystal structure, antibacterial activity and nanoparticles of Cd(II) complex derived from dithiophosphonate ligand. Phosphorus, Sulfur Silicon Relat. Elem. 2018; 193(6): 369-74.
- 24. Sağlam EG, Bulat E, Zeyrek CT, Dal H, Hökelek T. Syntheses of and structural studies on some square planar dithiophosphonato Ni(II) complexes, octahedral pyridine derivatives thereof and X-ray crystallography, DFT and molecular docking studies of the latter. J. Mol. Struc. 2019; 1178: 112–25.
- 25. Casas JS, García-Tasende MS, Sánchez A, Sordo J, Castellano EE, Zukerman-Schpector J. Synthesis, crystal structure and spectroscopic properties of bis(diphenyldithiophosphinato)cadmium(II). Inorg. Chim. Acta. 1994; 219(1–2): 115-19.
- 26. Shi W, Shafaei-Fallah M, Anson CE, Rothenberger A. Metal thiophosphonates and related compounds: an emerging area of supramolecular coordination chemistry. Dalton Trans. 2006; 26: 3257-62.
- 27. Czernuszewicz R, Maslowsky, E Jr, Nakamoto K. Infrared and Raman Spectra of Bis(imidotetraphenyldithiodiphosphino-S,S’) Complexes with Cu(II), Co(II) and Fe(II). Inorg. Chim. Acta. 1980; 40: 199-2.
- 28. Paddy JL, Lee NCJ, Waters DN, Trott W. Zinc Dialkyldithiophosphate Oxidation by Cumene Hydroperoxide: Kinetic Studies by Raman and 31P NMR Spectroscopy. J. Tribology Trans. 1990; 33(1): 15-20.
- 29. Larsson ML, Holmgren A. Reversible phase transition in Zn2(O,O-di(cyclohexyl)dithiophosphate)4, studied by Raman spectroscopy and compared with NMR results. Vib. Spectro. 2004; 34(2): 243-46.
- 30. Chakravarty M, Pailloux S, Ouizem S, Smith KA, Duesler EN, Paine RT, Williams NJ, Hancock RD. Synthesis and metal coordination chemistry of (phenyl)(pyridine-2-ylmethyl)phosphinodithioic acid. Polyhedron [2-C5H4N]CH2P(S)(SH)(Ph). 2012; 33: 327-35.
- 31. Karakuş M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russ. J. Coord Chem 2006; 32(6): 437–43.
- 32. Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von
Dithiophosphinsären. Phosphorus, Sulfur Silicon Relat. Elem. 1983; 14: 225-28.
- 33. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org. Mass Spectrom. 1984; 19: 82-86.
- 34. Karakuş M, Yılmaz H, Özcan Y, S İde. Appl. Crystallographic report: Bis{µ-[O-cyclopentyl (4-methoxyphenyl) dithiophosphonato] 1κ:S,2κ: S-[O-cyclopentyl(4-methoxyphenyl) dithiophosphonato]-1κ2S,S′}dicadmium(II). Organometal. Chem. 2004; 18: 141-42.
- 35. Ramirez RG, Toscano RA, Silverstru C, Haiduc I. Studies on inorganic tin diphenyldithiophosphinates. Crystal and molecular structure of CIS- dichlorobis(diphenyldithiophosphinato)tin(IV). Polyhedron 1996; 15(21): 3857–67.
- 36. Przychodzen W. New Products of Reaction of Lawesson's Reagent With Diols. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 1621–33.