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Syntheses and characterization of new dithiophosphinato zinc complexes

Yıl 2018, Cilt: 5 Sayı: 2, 931 - 940, 01.01.2018
https://doi.org/10.18596/jotcsa.427192

Öz

Four known dithiophosphinic
acids, DTPA, were synthesized and their zinc complexes were prepared as
novelties. The complexes have been proven to have the structures
[Zn(µ-DTPAn)2(DTPAn)2],
([DTPAn]= Rn(R)P(S)H, R= 4-CH3O-C6H4-;
R1= iso-amyl-, DTPA1; R2= iso-butyl-,
DTPA2; R3= sec-butyl-, DTPA3; R4=
iso-propyl-, DTPA4). The DTPAs were prepared by the reaction
of the
Lawesson
reagent, [2,4–bis(4-methoxyphenyl)–1,3,2,4–ditiyodifosfetan–2,4–disülfür] (LR),
with the corresponding Grignard compounds. The acids formed are viscous liquids
difficult to purify and so they were converted to ammonium salts,
[DTPAn][NH4],
which are easy to obtain as pure crystals. The complexes were identified to
have dimeric structures on the basis of mass spectroscopic data.

Kaynakça

  • 1. Mc.Cleverty J A, Rick S Z, Kowalski N, Bailey A, Mulvaney R, O'Cleirigh D A. Aspects of the Inorganic Chemistry of Rubber Vulcanisation. Part 4.1 Dialkyl- and Diaryl-dithiophosphate and –dithiophosphinate Complexes of Zinc: Phosphorus-31 Nuclear Magnetic Resonance Spectral Studies and Structures of [NMe4][Zn{S,P(OC6H4Me-p)2}3] and [Et4][Zn(S2PPh2)3]. J. Chem. Soc. Dalton Trans. 1983; 627-34. DOI 10.1039/DT9830000627.
  • 2. Satake Y, Kashiwadate K, Iizuka Y, Kouyama T, Katto T, Shiiki Z. Poly(arylene thioether-ketone) compositions improved in both melt stability and crystallinity. 1989: may 2; US 4,826,906.
  • 3. Pradip K G, Deba P P, Neeiotpal S. Di(2-methyl- 5-chlorophenyl) dithiophosphinate and its copper(II) derivative as antioxidant lubricating oil additive. Indian J. Chem. Technol. 1995; 2(1): 46-8. http://nopr.niscair.res.in/handle/123456789/31090.
  • 4. Ziyatdinova G K, Budnikov G K, Samigullin A I, Gabdullina G T, Sofronov A V, Al’metkina, L. A., Nizamov, I. S., Cherkasov, R. A.: Electrochemical determination of synthetic antioxidants of bisdithiophosphonic acids. J. Anal. Chem. 2010; 65: 1273–1279. DOI: 10.1134/S1061934810120129.
  • 5. Yagishita K, Konishi S. Lubricating oil additive and lubricating oil composition. 2013; US 8,481,467.
  • 6. Grigorieva N A, Pashkov G L, Fleitlikh I Yu, Nikiforova L K, Pleshkov M A. Nickel extraction from sulfate media with Cyanex 301 in the presence of electron donor additives. Hydrometallurgy 2010; 105: 82–8. DOI 10.1016/hydromet.2010.08.001.
  • 7. Xihong H, Guoxin T, Jing C, Linfeng R, Characterization of the extracted complexes of trivalent lanthanides with purified cyanex 301 incomparison with trivalent actinide complexes. Dalton Trans. 2014; 43: 17352–17357. DOI:10.1039/C4DT02553A.
  • 8. Jing C, Meng W, Xuegang L, Jianchen W. Back-end of nuclear fuel cycle in China. Progr. in Nucl. Energy, 2012; 54: 46-8, DOI:10.1016/j.pnucene.2011.09.003
  • 9. Artem'ev A V, Malysheva S F, Gusarova N K, Belogorlova N A, Fedorov S V, Timokhin B V, Smirnov V I, Trofimov B A. Novel Quinine, Lupinine, And Anabasine Derivatives Containing Dithiophosphinate Groups. Chem. Heterocycl. Compd. 2012 Jun; 48(3): 448-52. DOI:10.1007/s10593-012-1013-3.
  • 10. Michalski J, Potrzebowski M, Lopusinski A. Preparation of S-brom-dithiophosphoric, dithiophosphonic and dithiophosphinic acid derivatives, 1984; US 4,470,933.
  • 11. Kabra V, Mitharwal S, Singh S. Synthesis and Insecticidal Activity of Novel Dithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2009;184: 2431–42. DOI: 10.1080/10426500802487748
  • 12. Bara A C, Silvestru C, Haiduc I. Antitumor organometallics. I. Activity of some diphenyltin(IV) and diphenylantimony(III) derivatives on in vitro and in vivo Ehrlich ascites tumor. Anticancer Res. 11, 1651-1656, 1991.
  • 13. 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. DOI: 10.1016/0969-8051(94)00107-U.
  • 14. Durckheimer W, Bormann D, Ehlers E, Schrinner E, Heymes R. Cephem Derivates. 1988; US 4758556.
  • 15. Yordanov, N D, Gochev G, Angelova O, Macicek J. EPR Investigations on bis(dithiophosphinato)copper(II) complexes magnetically diluted in the corresponding nickel(II) single crystals and X-ray crystal structure of bis(di-n-propyldithiophosphinato)nickel(II). Polyhedron 1990; 9: 2597-2602. https://doi.org/10.1016/S0277-5387(00)86834-5.
  • 16. Byrom C, Malik M A, O’Brien P, White A J P, Williams D J. Synthesis and X-ray single crystal structures of bis(diisobutyldithiophosphinato)cadmium(II) or zinc(II): Potential single-source precursors for II/VI materials, Polyhedron, 2000; 19: 211-15.
  • 17. Calligaris M, Nardin G, Ripamonti A. Crystal and Molecular Structure of Zinc(II) and Cobalt(II) Diethyldithiophosphinates, J. Chem. Soc. A, 714-22, 1970. DOI: 10.1039/J19700000714.
  • 18. Sağlam E G, Çelik Ö, Yılmaz H, İde S. 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. Transition Met. Chem. 2010; 35: 399-405. DOI:10.1007/s11243-010-9341-6.
  • 19. Sağlam E G, Yılmaz H, Dal H, Hökelek T, Synthesis and Spectroscopic Characterizations of Novel Ni(II) and Co(II) Dithiophosphinate Complexes, and X-Ray Studies on the Ni(II) Complex Phosphorus, Sulfur Silicon Relat. Elem. 2012; (2)187: 213-24. DOI: 10.1080/10426507.2011.601239.
  • 20. Hoffmann H, Schumacher G, Umsetzungen mit p-methoxyphenyl-dithio-phosphonsäure-anhydrid, Tetrahedron Lett. 1967; 31:2963-6. DOI:10.1016/50040-4039(00)90895-5.
  • 21. Diemert K, Kuchen W. “Zur Kenntnis der Organophosphorverbindungen XVII, Dithiophosphinsauren RR’P(S)SH, Ihre Synthese, Derivate und MetallKomlexe”, Phosphorus, Sulfur Silicon Relat. Elem. 1977; (2): 131-6. DOI: 10.1080/03086647708077702.
  • 22. Casas J S, García-Tasende M S, Sánchez A, Sordo J, Castellano E E, Zukerman-Schpector J. Synthesis, crystal structure and spectroscopik properties of bis (diphenylditihiophosphinato)cadmium(II). Inorg. Chim. Acta 1994; 219: 115-9. DOI:10.1016/0020-1693(94)03822-8.
  • 23. Sunder S, Hanlan L, Bernstein J. Resonance Raman Spectra of Metal Complexes of Substituted Dithiophospinic Acids., J. Inorg. Chem. 1975;14: 2012-3, DOI: 10.1021/ic50150a058.
  • 24. 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: 199-202. DOI: 10.1016/S0020-1693(00)92004-8.
  • 25. Chakravarty M, Pailloux S, Ouizem S, Smith K A, Duesler E N, Paine R T, Williams N J, Hancock R D. Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl)phosphinodithioic acid, [2-C5H4N]CH2P(S)(SH)(Ph). 2012: 33: 327-35. DOI:10.1016/j.poly.2011.11.041.
  • 26. Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von Dithiophosphinsären, Phosphorus, Sulfur Silicon Relat. Elem., 1983; 14: 225-8. DOI:10.1080/03086648308075944.
  • 27. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org. Mass Spoctrom. 1984; 19: 82-6.DOI:10.1002/oms.120190207.
  • 28. Christoph D, Keck H, Kuchen W, Mathow J, Wunderlich H. Synthesis, properties and structure of bis(dialkyldithiophosphinato)manganese(II) complexes. Inorg. Chim. Acta 1987; 132,: 213-5. DOI:10.1016/S0020-1693(00)81744-2.
  • 29. Mohan P N, Keck H, Kuchen W, Haegele G. Metal complexes of phosphinic acids—XII: Praseodymium(III), neodymium(III) and europium(III) complexes of dimethyldithiophosphinic acid. J. Inorg. & Nuclear Chem. 1977; 39: 833-5. DOI:10.1016/0022-1902(77)80164-4.
  • 30. Sağlam E G, Nurcan A, Berline M-S, Hakan D, Tuncer H. Syntheses and Structural Characterizations of a New Benzyl(4-Methoxyphenyl)Dithiophosphinic Acid and Its Ni(II), Co(II), Zn(II), Cd(II) and Ni-Pyridino Complexes. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191(1): 22-9. DOI;10.1080/10426507.2015.1067206.
  • 31. 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: 396-7. DOI:10.1002/aoc.850.
  • 32. 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: 141-142.DOI: 10.1002/aoc.588.
  • 33. Ramirez R G, Toscano R A, Silverstu C, Haiduc I. Studies on inorganic tin diphenyldithiophosphinates. Crystal and molecular structure of CIS- dichlorobis(diphenyldithiophosphinato)tin(IV). Polyhedron 1996; 15(21): 3857–67.DOI:10.1016/0277-5387(96)00100-3.
  • 34. Karakuş M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Rus. J. Coord Chem 2006; 32(6): 437–43. DOI: 10.1134/S1070328406060078.
  • 35. Przychodzen W. New Products of Reaction of Lawesson's Reagent With Diols. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 1621–33. DOI:10.1080/10426500490466175.
Yıl 2018, Cilt: 5 Sayı: 2, 931 - 940, 01.01.2018
https://doi.org/10.18596/jotcsa.427192

Öz

Kaynakça

  • 1. Mc.Cleverty J A, Rick S Z, Kowalski N, Bailey A, Mulvaney R, O'Cleirigh D A. Aspects of the Inorganic Chemistry of Rubber Vulcanisation. Part 4.1 Dialkyl- and Diaryl-dithiophosphate and –dithiophosphinate Complexes of Zinc: Phosphorus-31 Nuclear Magnetic Resonance Spectral Studies and Structures of [NMe4][Zn{S,P(OC6H4Me-p)2}3] and [Et4][Zn(S2PPh2)3]. J. Chem. Soc. Dalton Trans. 1983; 627-34. DOI 10.1039/DT9830000627.
  • 2. Satake Y, Kashiwadate K, Iizuka Y, Kouyama T, Katto T, Shiiki Z. Poly(arylene thioether-ketone) compositions improved in both melt stability and crystallinity. 1989: may 2; US 4,826,906.
  • 3. Pradip K G, Deba P P, Neeiotpal S. Di(2-methyl- 5-chlorophenyl) dithiophosphinate and its copper(II) derivative as antioxidant lubricating oil additive. Indian J. Chem. Technol. 1995; 2(1): 46-8. http://nopr.niscair.res.in/handle/123456789/31090.
  • 4. Ziyatdinova G K, Budnikov G K, Samigullin A I, Gabdullina G T, Sofronov A V, Al’metkina, L. A., Nizamov, I. S., Cherkasov, R. A.: Electrochemical determination of synthetic antioxidants of bisdithiophosphonic acids. J. Anal. Chem. 2010; 65: 1273–1279. DOI: 10.1134/S1061934810120129.
  • 5. Yagishita K, Konishi S. Lubricating oil additive and lubricating oil composition. 2013; US 8,481,467.
  • 6. Grigorieva N A, Pashkov G L, Fleitlikh I Yu, Nikiforova L K, Pleshkov M A. Nickel extraction from sulfate media with Cyanex 301 in the presence of electron donor additives. Hydrometallurgy 2010; 105: 82–8. DOI 10.1016/hydromet.2010.08.001.
  • 7. Xihong H, Guoxin T, Jing C, Linfeng R, Characterization of the extracted complexes of trivalent lanthanides with purified cyanex 301 incomparison with trivalent actinide complexes. Dalton Trans. 2014; 43: 17352–17357. DOI:10.1039/C4DT02553A.
  • 8. Jing C, Meng W, Xuegang L, Jianchen W. Back-end of nuclear fuel cycle in China. Progr. in Nucl. Energy, 2012; 54: 46-8, DOI:10.1016/j.pnucene.2011.09.003
  • 9. Artem'ev A V, Malysheva S F, Gusarova N K, Belogorlova N A, Fedorov S V, Timokhin B V, Smirnov V I, Trofimov B A. Novel Quinine, Lupinine, And Anabasine Derivatives Containing Dithiophosphinate Groups. Chem. Heterocycl. Compd. 2012 Jun; 48(3): 448-52. DOI:10.1007/s10593-012-1013-3.
  • 10. Michalski J, Potrzebowski M, Lopusinski A. Preparation of S-brom-dithiophosphoric, dithiophosphonic and dithiophosphinic acid derivatives, 1984; US 4,470,933.
  • 11. Kabra V, Mitharwal S, Singh S. Synthesis and Insecticidal Activity of Novel Dithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2009;184: 2431–42. DOI: 10.1080/10426500802487748
  • 12. Bara A C, Silvestru C, Haiduc I. Antitumor organometallics. I. Activity of some diphenyltin(IV) and diphenylantimony(III) derivatives on in vitro and in vivo Ehrlich ascites tumor. Anticancer Res. 11, 1651-1656, 1991.
  • 13. 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. DOI: 10.1016/0969-8051(94)00107-U.
  • 14. Durckheimer W, Bormann D, Ehlers E, Schrinner E, Heymes R. Cephem Derivates. 1988; US 4758556.
  • 15. Yordanov, N D, Gochev G, Angelova O, Macicek J. EPR Investigations on bis(dithiophosphinato)copper(II) complexes magnetically diluted in the corresponding nickel(II) single crystals and X-ray crystal structure of bis(di-n-propyldithiophosphinato)nickel(II). Polyhedron 1990; 9: 2597-2602. https://doi.org/10.1016/S0277-5387(00)86834-5.
  • 16. Byrom C, Malik M A, O’Brien P, White A J P, Williams D J. Synthesis and X-ray single crystal structures of bis(diisobutyldithiophosphinato)cadmium(II) or zinc(II): Potential single-source precursors for II/VI materials, Polyhedron, 2000; 19: 211-15.
  • 17. Calligaris M, Nardin G, Ripamonti A. Crystal and Molecular Structure of Zinc(II) and Cobalt(II) Diethyldithiophosphinates, J. Chem. Soc. A, 714-22, 1970. DOI: 10.1039/J19700000714.
  • 18. Sağlam E G, Çelik Ö, Yılmaz H, İde S. 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. Transition Met. Chem. 2010; 35: 399-405. DOI:10.1007/s11243-010-9341-6.
  • 19. Sağlam E G, Yılmaz H, Dal H, Hökelek T, Synthesis and Spectroscopic Characterizations of Novel Ni(II) and Co(II) Dithiophosphinate Complexes, and X-Ray Studies on the Ni(II) Complex Phosphorus, Sulfur Silicon Relat. Elem. 2012; (2)187: 213-24. DOI: 10.1080/10426507.2011.601239.
  • 20. Hoffmann H, Schumacher G, Umsetzungen mit p-methoxyphenyl-dithio-phosphonsäure-anhydrid, Tetrahedron Lett. 1967; 31:2963-6. DOI:10.1016/50040-4039(00)90895-5.
  • 21. Diemert K, Kuchen W. “Zur Kenntnis der Organophosphorverbindungen XVII, Dithiophosphinsauren RR’P(S)SH, Ihre Synthese, Derivate und MetallKomlexe”, Phosphorus, Sulfur Silicon Relat. Elem. 1977; (2): 131-6. DOI: 10.1080/03086647708077702.
  • 22. Casas J S, García-Tasende M S, Sánchez A, Sordo J, Castellano E E, Zukerman-Schpector J. Synthesis, crystal structure and spectroscopik properties of bis (diphenylditihiophosphinato)cadmium(II). Inorg. Chim. Acta 1994; 219: 115-9. DOI:10.1016/0020-1693(94)03822-8.
  • 23. Sunder S, Hanlan L, Bernstein J. Resonance Raman Spectra of Metal Complexes of Substituted Dithiophospinic Acids., J. Inorg. Chem. 1975;14: 2012-3, DOI: 10.1021/ic50150a058.
  • 24. 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: 199-202. DOI: 10.1016/S0020-1693(00)92004-8.
  • 25. Chakravarty M, Pailloux S, Ouizem S, Smith K A, Duesler E N, Paine R T, Williams N J, Hancock R D. Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl)phosphinodithioic acid, [2-C5H4N]CH2P(S)(SH)(Ph). 2012: 33: 327-35. DOI:10.1016/j.poly.2011.11.041.
  • 26. Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von Dithiophosphinsären, Phosphorus, Sulfur Silicon Relat. Elem., 1983; 14: 225-8. DOI:10.1080/03086648308075944.
  • 27. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org. Mass Spoctrom. 1984; 19: 82-6.DOI:10.1002/oms.120190207.
  • 28. Christoph D, Keck H, Kuchen W, Mathow J, Wunderlich H. Synthesis, properties and structure of bis(dialkyldithiophosphinato)manganese(II) complexes. Inorg. Chim. Acta 1987; 132,: 213-5. DOI:10.1016/S0020-1693(00)81744-2.
  • 29. Mohan P N, Keck H, Kuchen W, Haegele G. Metal complexes of phosphinic acids—XII: Praseodymium(III), neodymium(III) and europium(III) complexes of dimethyldithiophosphinic acid. J. Inorg. & Nuclear Chem. 1977; 39: 833-5. DOI:10.1016/0022-1902(77)80164-4.
  • 30. Sağlam E G, Nurcan A, Berline M-S, Hakan D, Tuncer H. Syntheses and Structural Characterizations of a New Benzyl(4-Methoxyphenyl)Dithiophosphinic Acid and Its Ni(II), Co(II), Zn(II), Cd(II) and Ni-Pyridino Complexes. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191(1): 22-9. DOI;10.1080/10426507.2015.1067206.
  • 31. 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: 396-7. DOI:10.1002/aoc.850.
  • 32. 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: 141-142.DOI: 10.1002/aoc.588.
  • 33. Ramirez R G, Toscano R A, Silverstu C, Haiduc I. Studies on inorganic tin diphenyldithiophosphinates. Crystal and molecular structure of CIS- dichlorobis(diphenyldithiophosphinato)tin(IV). Polyhedron 1996; 15(21): 3857–67.DOI:10.1016/0277-5387(96)00100-3.
  • 34. Karakuş M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Rus. J. Coord Chem 2006; 32(6): 437–43. DOI: 10.1134/S1070328406060078.
  • 35. Przychodzen W. New Products of Reaction of Lawesson's Reagent With Diols. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 1621–33. DOI:10.1080/10426500490466175.
Toplam 35 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Makaleler
Yazarlar

Ertuğrul Gazi Sağlam 0000-0002-7719-3934

Nurcan Acar 0000-0003-3531-9073

Yayımlanma Tarihi 1 Ocak 2018
Gönderilme Tarihi 25 Mayıs 2018
Kabul Tarihi 30 Temmuz 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 5 Sayı: 2

Kaynak Göster

Vancouver Sağlam EG, Acar N. Syntheses and characterization of new dithiophosphinato zinc complexes. JOTCSA. 2018;5(2):931-40.