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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, , 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, , 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

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.