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.
REFERENCES
Wittig, G. and Geissler, G., Justus Liebigs Annalen der Chemie, 1953, vol. 580, p. 44.
Zykova, A.R.. Vestnik YuUrGU. Ser. Khim., 2020, vol. 12, no. 4, p. 5.
Sharutin, V.V., Poddel’skii, A.I., and Sharutina, O.K., Russ. J. Coord. Chem., 2020, vol. 46, no. 10, p. 663.
Sharutin, V.V. and Mosunova, T.V., Vestnik YuUrGU. Ser. Khim., 2020, vol. 12, no. 3, p. 7.
Razuvaev, G.A. and Osanova, N.A., Dokl. Akad. Nauk SSSR, 1955, vol. 104, no. 4, p. 552.
Razuvaev, G.A., Osanova, N.A., and Grigor’eva, I.K., Izv. Akad. Nauk SSSR. Ser. Khim., 1969, no. 10, p. 2234.
Sharutin, V.V., Pentaphenyl compounds of phosphorus, antimony, and bismuth and their derivatives. Possible applications in organic synthesis, Doctoral (Chem.) Dissertation, Irkutsk, 1995.
Sharutin, V.V., Zh. Obshch. Khim., 1988, vol. 58, no. 10, p. 2305.
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
Sharutin, V.V., Sharutina, O.K., Rybakova, A.V., and Gubanova, Yu.O., Russ. J. Gen. Chem., 2018, vol. 88, no. 8, p. 1629.
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
Sharutin, V.V., Molokova O.V., and Sharutina, O.K., Russ. J. Inorg. Chem., 2013, vol. 58, no. 4, p. 400.
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
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
Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., Russ. J. Coord. Chem., 2014, vol. 40, no. 2, p. 109.
Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., Russ. J. Inorg. Chem., 2017, vol. 62, no. 3, p. 295.
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
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
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
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
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.
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.
Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al., Russ. J. Gen. Chem., 2002, vol. 72, no. 3, p. 390.
Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al., Russ. J. Coord. Chem., 2001, vol. 27, no. 6, p. 393.
Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al., Russ. J. Coord. Chem., 2002, vol. 28, no. 5, p. 333.
Sharutin, V.V., Senchurin, V.S., Sharutina, O.K., et al., Russ. J. Gen. Chem., 2009, vol. 79, no. 10, p. 2131.
Sharutin, V.V. and Sharutina, O.K., Russ. J. Inorg. Chem., 2017, vol. 62, no. 7, p. 925.
Senchurin, V.S. and Orlenko, E.D., Vestnik YuUrGU. Ser. Khim., 2019, vol. 11, no. 2, p. 66.
Senchurin, V.S., Sharutin, V.V., Sharutina, O.K., Russ. J. Inorg. Chem., 2020, vol. 65, no. 3, p. 320.
Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., J. Struct. Chem., 2020, vol. 61, no. 5, p. 734.
Sharutin, V.V., Sharutina, O.K., and Senchurin, V.S., Russ. J. Inorg. Chem., 2020, vol. 65, no. 11, p. 1712.
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
Zhidkov, V.V., Sharutin, V.V., Bel’skii, V.K., and Magomedova, N.S., Zh. Obshch. Khim., 1995, vol. 65, no. 2, p. 251.
Sharutin, V.V., Bychkov, V.T., and Lebedev, V.A., Zh. Obshch. Khim., 1986, vol. 56, no. 2, p. 325.
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
Sharutin, V.V., Sharutina, O.K., Panova, L.P., and Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9, p. 1531.
Sharutin, V.V., Sharutina, O.K., Tarasova, T.A., et al., Zh. Obshch. Khim., 2000, vol. 70, no. 8, p. 1311.
Sharutin, V.V., Sharutina, O.K., Pakusina, A.P., et al., Russ. J. Coord. Chem., 2004, vol. 30, no. 1, p. 13.
Sharutin, V.V., Egorova, I.V., Pakusina, A.P., et al., Russ. J. Coord. Chem., 2007, vol. 33, no. 3, p. 168.
SMART and SAINT-Plus. Versions 5.0. Data Collection and Processing Software for the SMART System, Madison: Bruker AXS Inc., 1998.
SHELXTL/PC. Versions 5.10. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, Madison: Bruker AXS Inc., 1998.
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
Funding
The study did not receive any funding.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Additional information
Translated by E. Yablonskaya
Rights and permissions
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070328423700549