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A New Method for the Synthesis of Tetraorganylphosphonium Arenesulfonates [Ph3PR1][OSO2R2]

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Abstract

The interaction of equimolar amounts of tetraorganylphosphonium chlorides with naphthalene-1sulfonic, 2,5-dichlorobenzenesulfonic, 2,4-dinitrobenzenesulfonic, and 1-hydroxy-2,4-dinitronaphthalene-7-sulfonic acids in water has led to the formation of tetraorganylphosphonium arenesulfonates [Ph3PR1][OSO2R2]. The phosphorus atoms in the cations exhibit distorted tetrahedral coordination and arenesulfonate anions have their ordinary geometry with tetrahedral sulfur atom.

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REFERENCES

  1. Purdela, D. and Vilceanu, R., Chemistry of Organophosphorus Compounds, Bucharest: Editura Academici Republicii Socialiste România, 1965.

  2. Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., New York: Pergamon Press, 1982.

  3. Razuvaev, G.A., Osanova, N.A., Brilkina, T.G., Zinovjeva, T.I., and Sharutin, V.V., J. Organomet. Chem., 1975, vol. 99, no. 1, p. 93. https://doi.org/10.1016/S0022-328X(00)86365-2

    Article  CAS  Google Scholar 

  4. Wang, D. and Astruc, D., Chem. Rev., 2015, vol. 115, p. 6621. https://doi.org/10.1021/acs.chemrev.5b00203

    Article  CAS  PubMed  Google Scholar 

  5. Cordovilla, C., Bartolome, C., Martinez-Ilarduya, J.M., and Espinet, P., ACS Catal., 2015, vol. 5, p. 3040. https://doi.org/10.1021/acscatal.5b00448

    Article  CAS  Google Scholar 

  6. Chong, C.C., Hirao, H., and Kinjo, R., Angew. Chem. Int. Ed., 2015, vol. 127, p. 192. https://doi.org/10.1002/ange.201408760

    Article  Google Scholar 

  7. Sharutin, V.V., Sharutina, O.K., Rybakova, A.V., and Gubanova, Yu.O., Russ. J. Gen. Chem., 2018, vol. 88, no. 8, p. 1308. https://doi.org/10.1134/S0044460X18080139

    Article  Google Scholar 

  8. Sharutin, V.V., Mukusheva, N., and Urzhumova, A.V., Bull. South Ural State Univ., Ser. Chem., 2018, vol. 10, no. 2, p. 48. https://doi.org/10.14529/chem180206

    Article  Google Scholar 

  9. Sharutin, V.V., Sharutina, O.K., and Gubanova, Yu.O., Izv. Vuzov, Ser. Khim. Khim. Tekhnol, 2019, vol. 62, no. 2, p. 4. https://doi.org/10.6060/ivkkt.20196202.5823

    Article  CAS  Google Scholar 

  10. Akutsu, H., Masaki, K., Mori, K., Yamada, J., and Nakatsuji, S., Polyhedron, 2005, vol. 24, p. 2126. https://doi.org/10.1016/j.poly.2005.03.023

    Article  CAS  Google Scholar 

  11. Galpothdeniya, W.I.S., Fronczek, F.R., Cong, M., Bhattarai, N., Siraj, N., and Warner, I.M., J. Mater. Chem. (B), 2016, vol. 4, p. 1414. https://doi.org/10.1039/C5TB02038G

    Article  CAS  Google Scholar 

  12. Akutsu, H., Yamada, J., Nakatsuji, S., and Turner, S.S., Cryst. Eng. Commun., 2009, vol. 11, p. 2588. https://doi.org/10.1039/b909519e

    Article  CAS  Google Scholar 

  13. Onoda, A., Yamada, Y., Doi, M., Okamura, T., and Ueyama, N., Inorg. Chem., 2001, vol. 40, no. 3, p. 516. https://doi.org/10.1021/ic0003067

    Article  CAS  PubMed  Google Scholar 

  14. Akutsu, H., Ishihara, K., Ito, S., Nishiyama, F., Yamada, J., Nakatsuji, S., Turner, S.S., and Nakazawa, Y., Polyhedron, 2017, vol. 136, p. 23. https://doi.org/10.1016/j.poly.2017.02.001

    Article  CAS  Google Scholar 

  15. Camerel, F., Le Helloco, G., Guizouarn, T., Jeannin, O., Fourmigue, M., Frackowiak, A., Olejniczak, I., Swietlik, R., Marino, A., Collet, E., Toupet, L., Auban-Senzier, P., and Canadell, E., Cryst. Growth Des., 2013, vol. 13, no. 11, p. 5135. https://doi.org/10.1021/cg401416h

    Article  CAS  Google Scholar 

  16. Ferrer, E.G., Williams, P.A.M., Castellano, E.E., and Piro, O.E., Z. anorg. allg. Chem., 2002, vol. 628, p. 1979. https://doi.org/10.1002/1521-3749(200209)628:9/10<1979::AID-ZAAC1979>3.0.CO;2-V

    Article  CAS  Google Scholar 

  17. Tarasevich, B.N., IK-spektry osnovnykh klassov organicheskikh soedinenii (IR Spectra of the Main Classes of Organic Compounds), Moscow: MGU, 2012.

  18. Cordero, B., Gomez, V., Platero-Prats, A.E., Reves, M., Echeverria, J., Cremades, E., Barragan, F., and Alvarez, S., Dalton Trans., 2008, no. 21, p. 2832. https://doi.org/10.1039/B801115J

    Article  Google Scholar 

  19. Gillespie, P. and Hargittay, I., Model of Repulsion of Electron Pairs of the Valence Shell and the Structure of Molecules, Moscow: Mir, 1992.

  20. Ruther, R., Huber, F., and Preut, H., J. Organomet. Chem., 1985, vol. 295, no. 1, p. 21.

    Article  Google Scholar 

  21. Sharutin, V.V., Egorova, I.V., Ivanenko, T.K., Sharutina, O.K., and Popov, D.Yu., Koord. Khim., 2003, vol. 29, no. 7, p. 502.

    Google Scholar 

  22. Mantina, M., Chamberlin, A.C., Valero, R., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. (A), 2009, vol. 113, p. 5806. https://doi.org/10.1021/jp8111556

    Article  CAS  Google Scholar 

  23. SMART and SAINT-Plus. Version, 5.0. Data Collection and Processing Software for the SMART System. Madison (WI, USA): Bruker AXS Inc., 1998.

  24. SHELXTL/PC. Version 5.10. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data. Bruker AXS Inc., Madison: (WI, USA), 1998.

  25. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

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Sharutin, V.V., Sharutina, O.K. & Mekhanoshina, E.S. A New Method for the Synthesis of Tetraorganylphosphonium Arenesulfonates [Ph3PR1][OSO2R2]. Russ J Gen Chem 92, 969–976 (2022). https://doi.org/10.1134/S1070363222060081

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