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Year 2022, Volume 9, Issue 3, 183 - 191, 28.09.2022
https://doi.org/10.17350/HJSE19030000270

Abstract

References

  • Foreman MRStJ, Slawin AMZ, Woollins JD. 2,4-Diferrocenyl-1,3,dithiadiphosphetane 2,4 disulfide; structure and reactions with catechols and [PtCl2(PR3)2] (R = Et or Bun). Journal of the Chemical Society, Dalton Transactions, 18 (1996) 3653–3657.
  • 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, 7 (1990) 372.
  • Cortés-Santiago A, Navarrete-López AM, Vargas R. Garza J. Dissociation energy for the P2S2 ring in a family of thionation reagents and the corresponding chemical reactivity of separated species: a density functional theory analysis. Journal of Physical Organic Chemistry, 30 (5) (2016) 1–9.
  • Ziyatdinova GK, Budnikov GK, Samigullin AI, Gabdullina GT, Sofronov AV, Al'metkina LA, Nizamov IS, Cherkasov RA. Electrochemical Determination of Synthetic Antioxidants of Bisdithiophosphonic Acids. Journal of Analytical Chemistry, 65 (12) (2010) 1273-1279.
  • McCleverty JA, Kowalski RSZ, Bailey NA, Mulvaney R, O'Cleirigh DA. Aspects of the Inorganic Chemistry of Rubber Vulcanisation. Part 4. Dialkyl- and Diaryl-dithiophosphate and –dithiophosphinate Complexes of Zinc: Phosphorus-31 Nuclear Magnetic Resonance Spectral Studies and Structures of [NMe4][Zn{S2P(OC6H4Me-p)2}3] and [NEt4][Zn(S2PPh2)3]. Journal of the Chemical Society, Dalton Transactions, 4 (1983) 627-634.
  • Kabra V, Mitharwal S, Singh S. Synthesis and Insecticidal Activity of Novel Dithiophosphonates. Phosphorus, Sulfur Silicon, 184 (9) (2009) 2431-2442.
  • Banaei A, Saadat A, McArdle P, Goli MM. Crystal structure, antibacterial activity and nanoparticles of Cd(II) complex derived from dithiophosphonate ligand. Phosphorus, Sulfur Silicon, 193 (6) (2018) 369-3674.
  • Xihong H, Guoxin T, Jing C, Linfeng R. Characterization of the extracted complexes of trivalent lanthanides with purified cyanex 301 in comparison with trivalent actinide complexes. Journal of the Chemical Society, Dalton Transactions, 43 (2014) 17352-17357.
  • Wheatley PJ. An X-ray diffraction determination of the crystal and molecular structure of “methyl metadithiophosphonate [CH3·PS2]2. Journal of the Chemical Society, 0 (1962) 300–302.
  • Dimert K, Kuchen W. Synthesis of Dithiophosphinic Acids by Nucleophilic Fission of Perthiophosphonic Anhydrides. Angewandte Chemie International Edition, 10 (7) (1971) 508–509.
  • Aydemir C, Solak S, Doğanlı GA, Şensoy T, Arar D, Bozbeyoglu N, Dogan NM, Lönnecke P, Hey-Hawkins E, Şekerci M, Karakuş M. Synthesis, Characterization, and Antibacterial Activity of Dithiophosphonates and Amidodithiophosphonates. Phosphorus, Sulfur Silicon, 190 (3) (2015) 300–309.
  • Lecher HZ, Greenwood RA, Whitehouse KC, Chao TH. The Phosphonation of Aromatic compounds with Phosphorus Pentasulfide. Journal of the American Chemical Society, 78 (19) (1956) 5018–5022.
  • Karakuş M, Lönnecke P, Hey-Hawkins E. Zwitterionic ferrocenyldithiophosphonates: the molecular structure of [FcP(S)S(OCH2CH2NH2Me)] [Fc = Fe(η5-C5H4)( η5-C5H5)]. Polyhedron, 23 (2004) 2281–2284.
  • Sağlam EG, Bulat E, Yılmaz H. The Syntheses and Characterization of New Dithiophosphonates derived from Novel 2,4-Bis(methoxytolyl)-1,3-dithia-2,4-diphosphetane 2,4- disulfides and Their Ni(II) Complexes. Journal of the Turkish Chemical Society Section A: Chemistry, 7 (3) (2020) 789-800.
  • Sağlam EG, Bulat E, Acar N, Demirel I. New Homodinuclear Alkyl- and Aryl- Dithiophosphonato Cd(II) and Hg(II) complexes: Syntheses and Characterizations. Journal of the Turkish Chemical Society Section A: Chemistry, 7 (1) (2020) 49-64.
  • Aragoni MC, Arca M, Demartin F, Devillanova FA, 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. Journal of the Chemical Society, Dalton Transactions, 18 (2001) 2671–2677.
  • 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, [2-C5H4N]CH2P(S)(SH)(Ph). Polyhedron, 33 (2012) 327-35.
  • Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Organic Mass Spectrometry, 19 (1984) 82-86.
  • Karakuş M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russian Journal of Coordination Chemistry, 32 (6) (2006) 437–43.
  • Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von Dithiophosphinsären. Phosphorus, Sulfur Silicon, 14 (1983) 225-228.
  • 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. Journal of the Turkish Chemical Society Section A: Chemistry, 5(3) (2018) 1239-1248.
  • Sağlam EG, Acar N. Syntheses and characterization of new dithiophosphinato zinc complexes. Journal of the Turkish Chemical Society Section A: Chemistry, 5 (2) (2018) 931-940.
  • 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. Organic Magnetic Resonance, 9 (1) (1977) 35-43.

Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates

Year 2022, Volume 9, Issue 3, 183 - 191, 28.09.2022
https://doi.org/10.17350/HJSE19030000270

Abstract

In this study, perthiophosphonic acid anhydrides which are previously known (2,4-bis(3-methoxytolyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide ([(3-methoxytolyl)P(S)S)2], SAV-B1 reagent and 2,4-bis(ferrocenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide [(ferrocenyl)P(S)S)2], FcLR, Ferrocenyl Lawesson's Reagent) react with alcohols to obtain new dithiophosphonic acids (3-methoxytolyl=(CH3)(OCH3)C6H3- and Xn=alkyl group (R) for SAV-B1, HXn; R1=3-pentyl-, HX1; R2=2-butyl-, HX2; R3=2-pentyl-, HX3 and Fc=Ferrocenyl- and Yn=allkyl or aryl group (R’) for FcLR, HYn; R’1=4-tert-cyclohexyl-, HY1; R’2=2-phenyl-1-propyl-, HY2). These acids were then converted to ammonium salts ([NH4][Xn], [NH4][Yn]). The structures of ammonium salts were characterized by mass-(ESI), FT-IR, 1H-, 13C- and 31P-NMR spectroscopy and elemental analysis.

References

  • Foreman MRStJ, Slawin AMZ, Woollins JD. 2,4-Diferrocenyl-1,3,dithiadiphosphetane 2,4 disulfide; structure and reactions with catechols and [PtCl2(PR3)2] (R = Et or Bun). Journal of the Chemical Society, Dalton Transactions, 18 (1996) 3653–3657.
  • 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, 7 (1990) 372.
  • Cortés-Santiago A, Navarrete-López AM, Vargas R. Garza J. Dissociation energy for the P2S2 ring in a family of thionation reagents and the corresponding chemical reactivity of separated species: a density functional theory analysis. Journal of Physical Organic Chemistry, 30 (5) (2016) 1–9.
  • Ziyatdinova GK, Budnikov GK, Samigullin AI, Gabdullina GT, Sofronov AV, Al'metkina LA, Nizamov IS, Cherkasov RA. Electrochemical Determination of Synthetic Antioxidants of Bisdithiophosphonic Acids. Journal of Analytical Chemistry, 65 (12) (2010) 1273-1279.
  • McCleverty JA, Kowalski RSZ, Bailey NA, Mulvaney R, O'Cleirigh DA. Aspects of the Inorganic Chemistry of Rubber Vulcanisation. Part 4. Dialkyl- and Diaryl-dithiophosphate and –dithiophosphinate Complexes of Zinc: Phosphorus-31 Nuclear Magnetic Resonance Spectral Studies and Structures of [NMe4][Zn{S2P(OC6H4Me-p)2}3] and [NEt4][Zn(S2PPh2)3]. Journal of the Chemical Society, Dalton Transactions, 4 (1983) 627-634.
  • Kabra V, Mitharwal S, Singh S. Synthesis and Insecticidal Activity of Novel Dithiophosphonates. Phosphorus, Sulfur Silicon, 184 (9) (2009) 2431-2442.
  • Banaei A, Saadat A, McArdle P, Goli MM. Crystal structure, antibacterial activity and nanoparticles of Cd(II) complex derived from dithiophosphonate ligand. Phosphorus, Sulfur Silicon, 193 (6) (2018) 369-3674.
  • Xihong H, Guoxin T, Jing C, Linfeng R. Characterization of the extracted complexes of trivalent lanthanides with purified cyanex 301 in comparison with trivalent actinide complexes. Journal of the Chemical Society, Dalton Transactions, 43 (2014) 17352-17357.
  • Wheatley PJ. An X-ray diffraction determination of the crystal and molecular structure of “methyl metadithiophosphonate [CH3·PS2]2. Journal of the Chemical Society, 0 (1962) 300–302.
  • Dimert K, Kuchen W. Synthesis of Dithiophosphinic Acids by Nucleophilic Fission of Perthiophosphonic Anhydrides. Angewandte Chemie International Edition, 10 (7) (1971) 508–509.
  • Aydemir C, Solak S, Doğanlı GA, Şensoy T, Arar D, Bozbeyoglu N, Dogan NM, Lönnecke P, Hey-Hawkins E, Şekerci M, Karakuş M. Synthesis, Characterization, and Antibacterial Activity of Dithiophosphonates and Amidodithiophosphonates. Phosphorus, Sulfur Silicon, 190 (3) (2015) 300–309.
  • Lecher HZ, Greenwood RA, Whitehouse KC, Chao TH. The Phosphonation of Aromatic compounds with Phosphorus Pentasulfide. Journal of the American Chemical Society, 78 (19) (1956) 5018–5022.
  • Karakuş M, Lönnecke P, Hey-Hawkins E. Zwitterionic ferrocenyldithiophosphonates: the molecular structure of [FcP(S)S(OCH2CH2NH2Me)] [Fc = Fe(η5-C5H4)( η5-C5H5)]. Polyhedron, 23 (2004) 2281–2284.
  • Sağlam EG, Bulat E, Yılmaz H. The Syntheses and Characterization of New Dithiophosphonates derived from Novel 2,4-Bis(methoxytolyl)-1,3-dithia-2,4-diphosphetane 2,4- disulfides and Their Ni(II) Complexes. Journal of the Turkish Chemical Society Section A: Chemistry, 7 (3) (2020) 789-800.
  • Sağlam EG, Bulat E, Acar N, Demirel I. New Homodinuclear Alkyl- and Aryl- Dithiophosphonato Cd(II) and Hg(II) complexes: Syntheses and Characterizations. Journal of the Turkish Chemical Society Section A: Chemistry, 7 (1) (2020) 49-64.
  • Aragoni MC, Arca M, Demartin F, Devillanova FA, 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. Journal of the Chemical Society, Dalton Transactions, 18 (2001) 2671–2677.
  • 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, [2-C5H4N]CH2P(S)(SH)(Ph). Polyhedron, 33 (2012) 327-35.
  • Heinz S, Keck H, Kuchen W. Mass spectrometric studies of dithiophosphinato metal complexes. Organic Mass Spectrometry, 19 (1984) 82-86.
  • Karakuş M, Yılmaz H. Synthesis and Characterization of Ni(II), Zn(II), and Cd(II) Complexes with Dithiophosphonate Derivatives. Russian Journal of Coordination Chemistry, 32 (6) (2006) 437–43.
  • Keck H, Kuchen W. Massenspektrometrische Untersuchungen An Organophosphorverbindungen IV. Über den massenspektrometrischen Zerfall von Dithiophosphinsären. Phosphorus, Sulfur Silicon, 14 (1983) 225-228.
  • 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. Journal of the Turkish Chemical Society Section A: Chemistry, 5(3) (2018) 1239-1248.
  • Sağlam EG, Acar N. Syntheses and characterization of new dithiophosphinato zinc complexes. Journal of the Turkish Chemical Society Section A: Chemistry, 5 (2) (2018) 931-940.
  • 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. Organic Magnetic Resonance, 9 (1) (1977) 35-43.

Details

Primary Language English
Subjects Basic Sciences
Journal Section Research Articles
Authors

Ertuğrul Gazi SAĞLAM> (Primary Author)
MARMARA ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ, KİMYA BÖLÜMÜ
0000-0002-7719-3934
Türkiye


Elif BULAT>
MARMARA ÜNİVERSİTESİ, FEN BİLİMLERİ ENSTİTÜSÜ, KİMYA EĞİTİMİ (DR)
0000-0002-2164-3641
Türkiye


Ayşe YILDIRIM>
YOZGAT BOZOK ÜNİVERSİTESİ
0000-0001-7876-0745
Türkiye

Publication Date September 28, 2022
Application Date July 4, 2022
Acceptance Date August 1, 2022
Published in Issue Year 2022, Volume 9, Issue 3

Cite

Bibtex @research article { hjse1140299, journal = {Hittite Journal of Science and Engineering}, eissn = {2148-4171}, address = {Hitit Üniversitesi Mühendislik Fakültesi Kuzey Kampüsü Çevre Yolu Bulvarı 19030 Çorum / TÜRKİYE}, publisher = {Hitit University}, year = {2022}, volume = {9}, number = {3}, pages = {183 - 191}, doi = {10.17350/HJSE19030000270}, title = {Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates}, key = {cite}, author = {Sağlam, Ertuğrul Gazi and Bulat, Elif and Yıldırım, Ayşe} }
APA Sağlam, E. G. , Bulat, E. & Yıldırım, A. (2022). Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates . Hittite Journal of Science and Engineering , 9 (3) , 183-191 . DOI: 10.17350/HJSE19030000270
MLA Sağlam, E. G. , Bulat, E. , Yıldırım, A. "Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates" . Hittite Journal of Science and Engineering 9 (2022 ): 183-191 <https://dergipark.org.tr/en/pub/hjse/issue/72726/1140299>
Chicago Sağlam, E. G. , Bulat, E. , Yıldırım, A. "Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates". Hittite Journal of Science and Engineering 9 (2022 ): 183-191
RIS TY - JOUR T1 - Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates AU - Ertuğrul GaziSağlam, ElifBulat, AyşeYıldırım Y1 - 2022 PY - 2022 N1 - doi: 10.17350/HJSE19030000270 DO - 10.17350/HJSE19030000270 T2 - Hittite Journal of Science and Engineering JF - Journal JO - JOR SP - 183 EP - 191 VL - 9 IS - 3 SN - -2148-4171 M3 - doi: 10.17350/HJSE19030000270 UR - https://doi.org/10.17350/HJSE19030000270 Y2 - 2022 ER -
EndNote %0 Hittite Journal of Science and Engineering Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates %A Ertuğrul Gazi Sağlam , Elif Bulat , Ayşe Yıldırım %T Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates %D 2022 %J Hittite Journal of Science and Engineering %P -2148-4171 %V 9 %N 3 %R doi: 10.17350/HJSE19030000270 %U 10.17350/HJSE19030000270
ISNAD Sağlam, Ertuğrul Gazi , Bulat, Elif , Yıldırım, Ayşe . "Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates". Hittite Journal of Science and Engineering 9 / 3 (September 2022): 183-191 . https://doi.org/10.17350/HJSE19030000270
AMA Sağlam E. G. , Bulat E. , Yıldırım A. Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates. Hittite J Sci Eng. 2022; 9(3): 183-191.
Vancouver Sağlam E. G. , Bulat E. , Yıldırım A. Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates. Hittite Journal of Science and Engineering. 2022; 9(3): 183-191.
IEEE E. G. Sağlam , E. Bulat and A. Yıldırım , "Synthesis and Characterization of New Ferrocenyl and 3-methoxytolyl Dithiophosphonates", Hittite Journal of Science and Engineering, vol. 9, no. 3, pp. 183-191, Sep. 2022, doi:10.17350/HJSE19030000270