Syntheses and characterization of new dithiophosphinato zinc complexes

Year 2018, , 931 - 940, 01.01.2018

Ertuğrul Gazi Sağlam Nurcan Acar

https://doi.org/10.18596/jotcsa.427192

Cited By: 3

Abstract

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.

Keywords

Dithiophosphinic Acid, Dithiophosphinate, Phosphinodithioic Acid, Dithiophosphinato Zinc Complex, Lawesson’s Reagent

References

• 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.