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Syntheses and Spectroscopic Characterization on New [O–3-phenyl-1-propyl-(4-methoxyphenyl)dithiophosphonato] Ni(II), Cd(II) and Hg(II) Complexes

Year 2018, Volume: 5 Issue: 3, 1239 - 1248, 01.09.2018
https://doi.org/10.18596/jotcsa.468027

Abstract

In this study, four new
dithiophosphonic acid complexes, namely,
trans-bis-[O–3-phenyl-1-propyl-(4-methoxyphenyl) dithiophosphonato] nickel (II), {Bis-pyridine-bis-(O–3–phenylpropyl (4-methoxyphenyl) dithiophosphonato]} nickel (II), bis-{bis-( O–3-phenyl-1-propyl- (4-methoxyphenyl) dithiophosphonato] cadmium (II)} and bis - { bis - ( O–3 - phenyl – 1 - propyl- ( 4-methoxyphenyl
)
dithiophosphonato] mercury (II)} were syntheszed.
The complexes were of the general structure [Ni(L)2]
and
[M(µ-L)2(L)2], M= Cd2+ and Hg2+. The nickel(II) complex was
capable of coordinating two moles of pyridine per mole as many four-coordinated
nickel(II) complex do leading to the six-coordinated complex, [Ni(L)2(Py)2].



All the compounds were characterized by
elemental analysis; MS; FTIR and Raman spectroscopies. The
[Ni(L)2], [Cd(µ-L)2(L)2] and [Hg(µ-L)2(L)2]
were also
investigated by
1H-, 13C-
and 31P-NMR. The magnetic susceptibility of the pyridine nickel
complex was measured to confirm the hybridization patterns and the geometry.

References

  • 1. Fluck E, Binder H. Reaktionen der Perthiophosphonsäureanhydride mit Aminen und Ammoniak. Z. Anorg. Allg. Chem. 1970;377(3):298-304.
  • 2. Aragoni M C, M Arca, Demartin, F, Devillanova, F A, Graiff C, Isaia F, Lippolis V, Tiripicchio A, Verani G. Ring-Opening of Lawesson’s Reagent: New Syntheses of Phosphono- and Amidophosphono-Dithioato Complexes−Structural and CP-MAS 31P-NMR Characterization of [p-CH3OPh(X)PS2]2M (X = MeO, iPrNH; M = NiII, PdII, and PtII). Eur. J. Inorg. Chem. 2000;2000(10):2239-44.
  • 3. 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) dithiophosphinate] nickel(II) and bis [4-methoxyphenyl (3-methyl butyl) dithiophosphate]cobalt(II) complexes. Transition Met. Chem. 2010;35(4):399-405.
  • 4. Karakus M, Kara I, Çelik Ö, Orujalipoor I, İde S, Yılmaz H. Synthesis, characterization, single crystal structure and theoretical studies of trans-Ni(II)-complex with dithiophosphonate ligand. J. Mol. Struct. 2018;1163:128–36. 5. Karakus M, Yılmaz H, Bulak E. Synthesis and Characterization of Zn(II) and Cd(II) Complexes with Bisdithiophosphonates. Russian J. Coord. Chem. 2005;31(5):316–21.
  • 6. Dimitrov K, Rollet V, Saboni A, Alexandrova S. Separation of Cobalt and Nickel by Pertraction in a Rotating Film Contactor Using Cyanex 302 as a Carrier. Sep. Sci. Technol. 2005;40(10):2111–23.
  • 7. Colclough T. Role of additives and transition metals in lubricating oil oxidation. 1987; Ind. Eng. Chem. Res. 1987;26(9):1888-95.
  • 8. 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(12):1273–9.
  • 9. Kishore G M, Shah D M. Amino Acid Biosynthesis Inhibitors as Herbicides. Annu. Rev. Biochem. 1988;57:627-30.
  • 10. Kabra V, Mitharwal S, Singh S. Synthesis and Insecticidal Activity of Novel Dithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2009;184(9):2431–42.
  • 11. Cherkasov R A, Nizamov I S, Gabdullina G T, Almetkin, L A, Shamilov R R, Sofronov A V. Dithiophosphoric and Dithiophosphonic Acids and Their Derivatives on the Basis of Thymol: Synthesis and Antimicrobial Activity. Phosphorus, Sulfur Silicon Relat. Elem. 2013;188(1-3):33–5.
  • 12. Mckenna C E, Li Z-M, Ju J-Y, Pham P-T T, Kilkuskie R, Loo T L, Straw J. Simple and Conjugate Bifunctional Thiophosphonates: Synthesis and Potential as Anti-Viral Agents. Phosphorus, Sulfur Silicon Relat. Elem. 1993;74(1-4):469-70.
  • 13. Karakuş M, Ikiz Y, Kaya HI, Şimşek O. Synthesis, characterization, electrospinning and antibacterial studies on triphenylphosphinedithiphosphonates Copper(I) and Silver(I) complexes. Chem. Cent. J. 2014;8(18):18.
  • 14. Cherkasov R A, Nizamov I S, Martianov Y M, Almetkina L A, Nikitin Y N, Shamilov R R. Thiophosphorylation of Pharmacophoric Phenols, Diols, and Triols. Phosphorus, Sulfur Silicon Relat. Elem. 2013;188(1-3):24-6.
  • 15. Bara A, Socaciu C, Silvestru C, Haiduc I. Antitumor Organometallics. I. Activity of some diphenyltin(ıv) and diphenylantimony(ııı) derivatives on in vitro and in vivo ehrlich ascites tumor. Anticancer Res. 1991;11:1651–6.
  • 16. Van Zyl W E, Woollins J D. The coordination chemistry of dithiophosphonates: An emerging and versatile ligand class. Coord. Chem. Rev. 2013;257(3-4):718– 31.
  • 17. Liu H–L, Mao H-Y, Xu C, Zhang H-Y, Hou H-W, Wu Q-A, 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(10): 1799–804.
  • 18.Karakuş M, Lönnecke P, Hey-Hawkins E. Zwitterionic ferrocenyldithiophosphonates: the molecular structure of [FcP(S)S(OCH2CH2NH2Me)] [Fc = Fe(η5-C5H4)( η5-C5H5)]. Polyhedron. 2004;23(14):2281–4.
  • 19. Arca M, Cornia A, Devillanova F A, Fabretti A C, Isaia F, Lippolis V, Verani G. New perspectives in phosphonodithioate coordination chemistry. Synthesis and X-ray crystal structure of trans-bis-[O-ethyl-(4-methoxyphenyl)phosphonodithioato] nickel(II). Inorg. Chim. Acta. 1997;262(1):81–4.
  • 20. Blaurock S, Edelmann F T, Haiduc I, Mezei G, Poremba P. Dimeric thiophosphorus complexes of sodium and zinc: Structural characterization of [(THF)2NaO(S)PPh2]2 and [Zn{S2P(OMe)C6H4OEt-p}2]2. Inorg. Chim. Acta 2008;361(1): 407–10.
  • 21. Aragoni M C, Arca M, Demartin F, Devillanova F A, Graiff C, Isaia F, Lippolis V, Tiripicchio A, Verani G. Reactivity of phosphonodithioato NiII complexes: solution equilibria, solid state studies and theoretical calculations on the adduct formation with some pyridine derivatives. J. Chem. Soc., Dalton Trans. 2001;18:2671–7.
  • 22.Sewpersad S, Van Zyl W E. Bis[μ-O-isopropyl(4-ethoxyphenyl)- dithiophosphonato - κ 2S : S’] bis { (O-isopropyl(4-ethoxyphenyl) dithiophosphonato- κ2S:S’] mercury(II)}. Acta Cryst. 2012;E68:m1488–9.
  • 23. Karakus M, Yilmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russian J. Coord. Chem. 2006;32(6):437–43.
  • 24. Van Zyl W E, Facler J P: A General and Convenient Route to Dithiophosphonate Salt Derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 2000;167(1):117-32.
  • 25. Sağlam E G, Erden S, Tutsak Ö, Eskiköy Bayraktepe D, Durmuş Z, Dal H, Ebinç A. Syntheses, characterization of and studies on the electrochemical behaviour of ferrocenyl dithiophosphonates and 4-methoxyphenyl dithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2017;192(3):322-9.
  • 26. Sağlam E G, Çelik Ö, İde S, Yılmaz H. Synthesis and Determination of Crystal and Molecular Structure of {Bispyridine-bis(4-methoxyphenyl(3-methylbutyl)dithiophosphinato]}nickel(II). Japan Soc. Anal. Chem. X-ray Struct. Anal. Online 2011;27:23-4.
  • 27. 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). Polyhedron. 2012;33(1):327-35.
  • 28. Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von Dithiophosphinsären, Phosphorus, Sulfur Silicon Relat. Elem. 1983;14(2): 225-8.
  • 29. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org. Mass Spoctrom.1984;19:82-6. 30. 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(5):833-5.
  • 31.Sundee S, Hanlan L, Bernstein J. Resonance Raman Spectra of Metal Complexes of Substituted Dithiophosphinic acids. Inorg. Chem. 1975;14:2012-3.
  • 32. 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(1-2):115-9.
  • 33.Noji M, Kidani Y, Koike H. Studies Bivalent Metal Chelates of 2-Aminomethylpyridine. Bull. Chem. Soc. Japan. 1975;48:245-9.
  • 34. 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.
  • 35. 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(3):396-7.
  • 36. Sağlam E G, Acar N. JOTCSA. Syntheses and characterization of new dithiophosphinato zinc complexes. 2018;5(2):931-40.
  • 37. Ernst L. 13C-N.m.r. Spectroscopy of Diethyl Alkyl- and Benzyl-phosphonates. A Study of Phosphorus-Carbon Spin-Spin Coupling Constants over One to Seven Bonds. Org. Magn. Reson. 1977;9(1):35-43.
  • 38. Karakuş M, Solak S, Hökelek T, Dal H, Bayrakdal A, Özdemir Kart S, Karabacak M, Kart H H: Synthesis, crystal structure and ab initio/DFT calculations of a derivative of dithiophosphonates. Spectrochim. Acta. Part A. 2014;122:582–90.
Year 2018, Volume: 5 Issue: 3, 1239 - 1248, 01.09.2018
https://doi.org/10.18596/jotcsa.468027

Abstract

References

  • 1. Fluck E, Binder H. Reaktionen der Perthiophosphonsäureanhydride mit Aminen und Ammoniak. Z. Anorg. Allg. Chem. 1970;377(3):298-304.
  • 2. Aragoni M C, M Arca, Demartin, F, Devillanova, F A, Graiff C, Isaia F, Lippolis V, Tiripicchio A, Verani G. Ring-Opening of Lawesson’s Reagent: New Syntheses of Phosphono- and Amidophosphono-Dithioato Complexes−Structural and CP-MAS 31P-NMR Characterization of [p-CH3OPh(X)PS2]2M (X = MeO, iPrNH; M = NiII, PdII, and PtII). Eur. J. Inorg. Chem. 2000;2000(10):2239-44.
  • 3. 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) dithiophosphinate] nickel(II) and bis [4-methoxyphenyl (3-methyl butyl) dithiophosphate]cobalt(II) complexes. Transition Met. Chem. 2010;35(4):399-405.
  • 4. Karakus M, Kara I, Çelik Ö, Orujalipoor I, İde S, Yılmaz H. Synthesis, characterization, single crystal structure and theoretical studies of trans-Ni(II)-complex with dithiophosphonate ligand. J. Mol. Struct. 2018;1163:128–36. 5. Karakus M, Yılmaz H, Bulak E. Synthesis and Characterization of Zn(II) and Cd(II) Complexes with Bisdithiophosphonates. Russian J. Coord. Chem. 2005;31(5):316–21.
  • 6. Dimitrov K, Rollet V, Saboni A, Alexandrova S. Separation of Cobalt and Nickel by Pertraction in a Rotating Film Contactor Using Cyanex 302 as a Carrier. Sep. Sci. Technol. 2005;40(10):2111–23.
  • 7. Colclough T. Role of additives and transition metals in lubricating oil oxidation. 1987; Ind. Eng. Chem. Res. 1987;26(9):1888-95.
  • 8. 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(12):1273–9.
  • 9. Kishore G M, Shah D M. Amino Acid Biosynthesis Inhibitors as Herbicides. Annu. Rev. Biochem. 1988;57:627-30.
  • 10. Kabra V, Mitharwal S, Singh S. Synthesis and Insecticidal Activity of Novel Dithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2009;184(9):2431–42.
  • 11. Cherkasov R A, Nizamov I S, Gabdullina G T, Almetkin, L A, Shamilov R R, Sofronov A V. Dithiophosphoric and Dithiophosphonic Acids and Their Derivatives on the Basis of Thymol: Synthesis and Antimicrobial Activity. Phosphorus, Sulfur Silicon Relat. Elem. 2013;188(1-3):33–5.
  • 12. Mckenna C E, Li Z-M, Ju J-Y, Pham P-T T, Kilkuskie R, Loo T L, Straw J. Simple and Conjugate Bifunctional Thiophosphonates: Synthesis and Potential as Anti-Viral Agents. Phosphorus, Sulfur Silicon Relat. Elem. 1993;74(1-4):469-70.
  • 13. Karakuş M, Ikiz Y, Kaya HI, Şimşek O. Synthesis, characterization, electrospinning and antibacterial studies on triphenylphosphinedithiphosphonates Copper(I) and Silver(I) complexes. Chem. Cent. J. 2014;8(18):18.
  • 14. Cherkasov R A, Nizamov I S, Martianov Y M, Almetkina L A, Nikitin Y N, Shamilov R R. Thiophosphorylation of Pharmacophoric Phenols, Diols, and Triols. Phosphorus, Sulfur Silicon Relat. Elem. 2013;188(1-3):24-6.
  • 15. Bara A, Socaciu C, Silvestru C, Haiduc I. Antitumor Organometallics. I. Activity of some diphenyltin(ıv) and diphenylantimony(ııı) derivatives on in vitro and in vivo ehrlich ascites tumor. Anticancer Res. 1991;11:1651–6.
  • 16. Van Zyl W E, Woollins J D. The coordination chemistry of dithiophosphonates: An emerging and versatile ligand class. Coord. Chem. Rev. 2013;257(3-4):718– 31.
  • 17. Liu H–L, Mao H-Y, Xu C, Zhang H-Y, Hou H-W, Wu Q-A, 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(10): 1799–804.
  • 18.Karakuş M, Lönnecke P, Hey-Hawkins E. Zwitterionic ferrocenyldithiophosphonates: the molecular structure of [FcP(S)S(OCH2CH2NH2Me)] [Fc = Fe(η5-C5H4)( η5-C5H5)]. Polyhedron. 2004;23(14):2281–4.
  • 19. Arca M, Cornia A, Devillanova F A, Fabretti A C, Isaia F, Lippolis V, Verani G. New perspectives in phosphonodithioate coordination chemistry. Synthesis and X-ray crystal structure of trans-bis-[O-ethyl-(4-methoxyphenyl)phosphonodithioato] nickel(II). Inorg. Chim. Acta. 1997;262(1):81–4.
  • 20. Blaurock S, Edelmann F T, Haiduc I, Mezei G, Poremba P. Dimeric thiophosphorus complexes of sodium and zinc: Structural characterization of [(THF)2NaO(S)PPh2]2 and [Zn{S2P(OMe)C6H4OEt-p}2]2. Inorg. Chim. Acta 2008;361(1): 407–10.
  • 21. Aragoni M C, Arca M, Demartin F, Devillanova F A, Graiff C, Isaia F, Lippolis V, Tiripicchio A, Verani G. Reactivity of phosphonodithioato NiII complexes: solution equilibria, solid state studies and theoretical calculations on the adduct formation with some pyridine derivatives. J. Chem. Soc., Dalton Trans. 2001;18:2671–7.
  • 22.Sewpersad S, Van Zyl W E. Bis[μ-O-isopropyl(4-ethoxyphenyl)- dithiophosphonato - κ 2S : S’] bis { (O-isopropyl(4-ethoxyphenyl) dithiophosphonato- κ2S:S’] mercury(II)}. Acta Cryst. 2012;E68:m1488–9.
  • 23. Karakus M, Yilmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russian J. Coord. Chem. 2006;32(6):437–43.
  • 24. Van Zyl W E, Facler J P: A General and Convenient Route to Dithiophosphonate Salt Derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 2000;167(1):117-32.
  • 25. Sağlam E G, Erden S, Tutsak Ö, Eskiköy Bayraktepe D, Durmuş Z, Dal H, Ebinç A. Syntheses, characterization of and studies on the electrochemical behaviour of ferrocenyl dithiophosphonates and 4-methoxyphenyl dithiophosphonates. Phosphorus, Sulfur Silicon Relat. Elem. 2017;192(3):322-9.
  • 26. Sağlam E G, Çelik Ö, İde S, Yılmaz H. Synthesis and Determination of Crystal and Molecular Structure of {Bispyridine-bis(4-methoxyphenyl(3-methylbutyl)dithiophosphinato]}nickel(II). Japan Soc. Anal. Chem. X-ray Struct. Anal. Online 2011;27:23-4.
  • 27. 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). Polyhedron. 2012;33(1):327-35.
  • 28. Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von Dithiophosphinsären, Phosphorus, Sulfur Silicon Relat. Elem. 1983;14(2): 225-8.
  • 29. Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Org. Mass Spoctrom.1984;19:82-6. 30. 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(5):833-5.
  • 31.Sundee S, Hanlan L, Bernstein J. Resonance Raman Spectra of Metal Complexes of Substituted Dithiophosphinic acids. Inorg. Chem. 1975;14:2012-3.
  • 32. 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(1-2):115-9.
  • 33.Noji M, Kidani Y, Koike H. Studies Bivalent Metal Chelates of 2-Aminomethylpyridine. Bull. Chem. Soc. Japan. 1975;48:245-9.
  • 34. 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.
  • 35. 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(3):396-7.
  • 36. Sağlam E G, Acar N. JOTCSA. Syntheses and characterization of new dithiophosphinato zinc complexes. 2018;5(2):931-40.
  • 37. Ernst L. 13C-N.m.r. Spectroscopy of Diethyl Alkyl- and Benzyl-phosphonates. A Study of Phosphorus-Carbon Spin-Spin Coupling Constants over One to Seven Bonds. Org. Magn. Reson. 1977;9(1):35-43.
  • 38. Karakuş M, Solak S, Hökelek T, Dal H, Bayrakdal A, Özdemir Kart S, Karabacak M, Kart H H: Synthesis, crystal structure and ab initio/DFT calculations of a derivative of dithiophosphonates. Spectrochim. Acta. Part A. 2014;122:582–90.
There are 36 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Ertuğrul Gazi Sağlam 0000-0002-7719-3934

Ahmet Ebinç This is me

Publication Date September 1, 2018
Submission Date October 7, 2018
Acceptance Date October 23, 2018
Published in Issue Year 2018 Volume: 5 Issue: 3

Cite

Vancouver Sağlam EG, Ebinç A. Syntheses and Spectroscopic Characterization on New [O–3-phenyl-1-propyl-(4-methoxyphenyl)dithiophosphonato] Ni(II), Cd(II) and Hg(II) Complexes. JOTCSA. 2018;5(3):1239-48.