Skip to main content
Log in

Tetraphenylphosphorus and Tetraphenylantimony (2-Carboxy)benzenesulfonates: Synthesis and Structures

  • Published:
Russian Journal of Coordination Chemistry Aims and scope Submit manuscript

Abstract

The reactions of pentaphenylphosphorus and pentaphenylantimony with 2-sulfobenzoic acid in benzene afford tetraphenylphosphonium [Ph4P]+[OSO2C6H4(COOH-2)] (I) and tetraphenylstibonium [Ph4Sb]+[OSO2C6H4(COOH-2)] (II) (2-carboxy)benzenesulfonates in the yield up to 90%. Compounds I and II are also synthesized from tetraphenylphosphonium and tetraphenylstibonium chlorides and 2-sulfobenzoic acid in water in the yield up to 89%. The complexes are characterized by X-ray diffraction (XRD) (CIF files CCDC nos. 2144288 (I) and 2123516 (II)) and IR spectroscopy.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.

REFERENCES

  1. Wittig, G. and Geissler, G., Justus Liebigs Annalen der Chemie, 1953, vol. 580, p. 44.

  2. Zykova, A.R.. Vestnik YuUrGU. Ser. Khim., 2020, vol. 12, no. 4, p. 5.

    Google Scholar 

  3. Sharutin, V.V., Poddel’skii, A.I., and Sharutina, O.K., Russ. J. Coord. Chem., 2020, vol. 46, no. 10, p. 663.

    Article  CAS  Google Scholar 

  4. Sharutin, V.V. and Mosunova, T.V., Vestnik YuUrGU. Ser. Khim., 2020, vol. 12, no. 3, p. 7.

    Google Scholar 

  5. Razuvaev, G.A. and Osanova, N.A., Dokl. Akad. Nauk SSSR, 1955, vol. 104, no. 4, p. 552.

    CAS  Google Scholar 

  6. Razuvaev, G.A., Osanova, N.A., and Grigor’eva, I.K., Izv. Akad. Nauk SSSR. Ser. Khim., 1969, no. 10, p. 2234.

  7. Sharutin, V.V., Pentaphenyl compounds of phosphorus, antimony, and bismuth and their derivatives. Possible applications in organic synthesis, Doctoral (Chem.) Dissertation, Irkutsk, 1995.

  8. Sharutin, V.V., Zh. Obshch. Khim., 1988, vol. 58, no. 10, p. 2305.

    CAS  Google Scholar 

  9. Sharutin, V.V., Senchurin, V.S., and Sharutina, O.K., Russ. J. Gen. Chem., 2009, vol. 79, no. 1. p. 78. https://doi.org/10.1134/S1070363209010125

    Article  CAS  Google Scholar 

  10. Sharutin, V.V., Sharutina, O.K., Rybakova, A.V., and Gubanova, Yu.O., Russ. J. Gen. Chem., 2018, vol. 88, no. 8, p. 1629.

    Article  CAS  Google Scholar 

  11. Li, J.-S., Liu, R.-C., Chi, X.-B., et al., Inorg. Chim. Acta, 2004, vol. 357, no. 7, p. 2176. https://doi.org/10.1016/j.ica.2003.12.012

    Article  CAS  Google Scholar 

  12. Sharutin, V.V., Molokova O.V., and Sharutina, O.K., Russ. J. Inorg. Chem., 2013, vol. 58, no. 4, p. 400.

    Article  CAS  Google Scholar 

  13. Ma, C., Zhang, Q., Sun, J., and Zhang, R., J. Organomet. Chem., 2006, vol. 691, no. 11, p. 2567. https://doi.org/10.1016/j.jorganchem.2006.01.049

    Article  CAS  Google Scholar 

  14. Arvanitis, G.M., Berardini, M.E., Acton, T.B., and Dumas, P.E., Phosphorus, Sulfur Silicon, Relat. Elem., 1993, vol. 82, nos. 1–4, p. 127. https://doi.org/10.1080/10426509308047416

    Article  CAS  Google Scholar 

  15. Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., Russ. J. Coord. Chem., 2014, vol. 40, no. 2, p. 109.

    Article  CAS  Google Scholar 

  16. Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., Russ. J. Inorg. Chem., 2017, vol. 62, no. 3, p. 295.

    Article  CAS  Google Scholar 

  17. Sharutin, V.V., Sharutina, O.K., Gubanova, Y.O., and Eltsov, O.S., Inorg. Chim. Acta, 2019, vol. 494, p. 211. https://doi.org/10.1016/j.ica.2019.05.029

    Article  CAS  Google Scholar 

  18. Liu, R.-C., Ma, Y.-Q., Yu, L., et al., Appl. Organomet. Chem., 2003, vol. 17, no. 9, p. 662. https://doi.org/10.1002/aoc.491

    Article  CAS  Google Scholar 

  19. Li, J.-S., Ma, Y.-Q., Cui, J.-R., and Wang, R.-Q., Appl. Organomet. Chem., 2001, vol. 15, no. 7, p. 639. https://doi.org/10.1002/aoc.200

    Article  CAS  Google Scholar 

  20. Quan, L., Yin, H., Cui, J., et al., J. Organomet. Chem., 2009, vol. 694, no. 23, p. 3683. https://doi.org/10.1016/j.jorganchem.2009.07.041

    Article  CAS  Google Scholar 

  21. Sharutin, V.V., Sharutina, O.K., Efremov, A.N., and Artem’eva, E.V., Russ. J. Inorg. Chem., 2019, vol. 64, no. 10, p. 1229.

    Article  CAS  Google Scholar 

  22. Sharutin, V.V., Sharutina, O.K., Efremov, A.N., and Artem’eva, E.V., Russ. J. Inorg. Chem., 2020, vol. 65, no. 4, p. 502.

    Article  CAS  Google Scholar 

  23. Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al., Russ. J. Gen. Chem., 2002, vol. 72, no. 3, p. 390.

    Article  CAS  Google Scholar 

  24. Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al., Russ. J. Coord. Chem., 2001, vol. 27, no. 6, p. 393.

    Article  CAS  Google Scholar 

  25. Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al., Russ. J. Coord. Chem., 2002, vol. 28, no. 5, p. 333.

    Article  CAS  Google Scholar 

  26. Sharutin, V.V., Senchurin, V.S., Sharutina, O.K., et al., Russ. J. Gen. Chem., 2009, vol. 79, no. 10, p. 2131.

    Article  CAS  Google Scholar 

  27. Sharutin, V.V. and Sharutina, O.K., Russ. J. Inorg. Chem., 2017, vol. 62, no. 7, p. 925.

    Article  Google Scholar 

  28. Senchurin, V.S. and Orlenko, E.D., Vestnik YuUrGU. Ser. Khim., 2019, vol. 11, no. 2, p. 66.

    Google Scholar 

  29. Senchurin, V.S., Sharutin, V.V., Sharutina, O.K., Russ. J. Inorg. Chem., 2020, vol. 65, no. 3, p. 320.

    Article  Google Scholar 

  30. Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., J. Struct. Chem., 2020, vol. 61, no. 5, p. 734.

    Article  CAS  Google Scholar 

  31. Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., Russ. J. Inorg. Chem., 2020, vol. 65, no. 11, p. 1712.

    Article  Google Scholar 

  32. Razuvaev, G.A., Osanova, N.A., Brilkina, T.G., et al., J. Organomet. Chem., 1975, vol. 99, no. 1, p. 93. https://doi.org/10.1016/S0022-328X(00)8636

    Article  CAS  Google Scholar 

  33. Zhidkov, V.V., Sharutin, V.V., Bel’skii, V.K., and Magomedova, N.S., Zh. Obshch. Khim., 1995, vol. 65, no. 2, p. 251.

    CAS  Google Scholar 

  34. Sharutin, V.V., Bychkov, V.T., and Lebedev, V.A., Zh. Obshch. Khim., 1986, vol. 56, no. 2, p. 325.

    CAS  Google Scholar 

  35. Ruther, R., Huber, F., and Preut, H., J. Organomet. Chem., 1985, vol. 295, no. 1, p. 21. https://doi.org/10.1016/0022-328X(85)88068-2

    Article  Google Scholar 

  36. Sharutin, V.V., Sharutina, O.K., Panova, L.P., and Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9, p. 1531.

    Google Scholar 

  37. Sharutin, V.V., Sharutina, O.K., Tarasova, T.A., et al., Zh. Obshch. Khim., 2000, vol. 70, no. 8, p. 1311.

    Google Scholar 

  38. Sharutin, V.V., Sharutina, O.K., Pakusina, A.P., et al., Russ. J. Coord. Chem., 2004, vol. 30, no. 1, p. 13.

    Article  CAS  Google Scholar 

  39. Sharutin, V.V., Egorova, I.V., Pakusina, A.P., et al., Russ. J. Coord. Chem., 2007, vol. 33, no. 3, p. 168.

    Article  CAS  Google Scholar 

  40. SMART and SAINT-Plus. Versions 5.0. Data Collection and Processing Software for the SMART System, Madison: Bruker AXS Inc., 1998.

  41. SHELXTL/PC. Versions 5.10. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, Madison: Bruker AXS Inc., 1998.

  42. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., et al., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

Download references

Funding

The study did not receive any funding.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. V. Sharutin.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Translated by E. Yablonskaya

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Efremov, A.N., Sharutin, V.V. Tetraphenylphosphorus and Tetraphenylantimony (2-Carboxy)benzenesulfonates: Synthesis and Structures. Russ J Coord Chem 49, 318–323 (2023). https://doi.org/10.1134/S1070328423700549

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070328423700549

Keywords:

Navigation