Skip to main content
SpringerLink
Log in

A STUDY OF CRYSTAL STRUCTURES OF ORGANYL-TRIPHENYLPHOSPHONIUM 2,4-DINITROBENZENE SULPHONATES [Ph3PR][OSO2C6H3(NO2)2-2,4], R = CH2OMe, CH2CN, CH2CH = CHCH2PPh3

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

Ionic organyl-triphenylphosphonium 2,4-dinitrobenzenesulfonates [Ph3PR][OSO2C6H3(NO2)2-2,4], R = CH2OMe (1), CH2CN (2), CH2CH = CHCH2PPh3 (3) are prepared by the reaction of organyl-triphenylphosphonium halides with 2,4-dinitrobenzenesulfonic acid in water and are structurally characterized. According to the XRD data, the phosphorus atoms in cations 1-3 have a distorted tetrahedral coordination, the sulfonate anions have a usual geometry with a sulfur atom in a tetrahedral environment. The lengths of P–C bonds vary within 1.742(2)-1.872(2) Å; the CPC bond angles fall within 104.92(6)-113.43(11)°. In the arenesulfonate anions of the complexes, the S–C distances are close to each other (1.743(2)-1.806(3) Å), all the S–O bonds are almost equal (1.4324(15)-1.477(2) Å). The [Ph3PCH2CH=CHCH2PPh3]+ cations of complex 3 contain second-order rotation-reflection axes passing through the centers of the C=C double bonds (point group C2h). The structures of 1, 3 contain short CAr⋯H(Ph) contacts (CH⋯π interactions) (2.829 Å (1), 2.769 Å (3)). The structures of 1-3 are mainly determined by weak intermolecular O⋯H contacts 2.30-2.61 Å (1), 2.23-2.68 Å (2), 2.35-2.69 Å (3).

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

REFERENCES

  1. F. R. Hartley. The Chemistry of Organophosphorus Compounds, Vol. 3: Phosphonium Salts, Ylides and Phosphoranes. John Wiley & Sons, 1993.

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  5. M. Matsumiya, D. Nomizu, Y. Tsuchida, and Y. Sasaki. Solvent Extr. Ion Exch., 2021, 39, 764. https://doi.org/10.1080/07366299.2021.1889761

    Article  CAS  Google Scholar 

  6. G. A. Razuvaev, N. A. Osanova, T. G. Brilkina, T. I. Zinovjeva, and V. V. Sharutin. J. Organomet. Chem., 1975, 99, 93. https://doi.org/10.1016/S0022-328X(00)86365-2

    Article  CAS  Google Scholar 

  7. D. Barton and W. D. Ollis. Comprehensive Organic Chemistry, Vol. 2: Phosphorus Compounds. Oxford, UK: Pergamon, 1979.

  8. C. G. Cassity, A. Mirjafari, N. Mobarrez, K. J. Strickland, R. A. OBrien, and J. H. Davis. Chem. Commun., 2013, 49, 7590. https://doi.org/10.1039/c3cc44118k

    Article  CAS  Google Scholar 

  9. M. Milenkovic, B. Warzajtis, U. Rychlewska, D. Radanovic, K. Andelkovic, T. Bozic, M. Vujcic, and D. Sladic. Molecules, 2012, 17, 2567. https://doi.org/10.3390/molecules17032567

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. J. A. Pavlova, Z. Z. Khairullina, A. G. Tereshchenkov, P. A. Nazarov, D. A. Lukianov, I. A. Volynkina, D. A. Skvortsov, G. I. Makarov, E. Abad, S. Y. Murayama, S. Kajiwara, A. Paleskava, A. L. Konevega, Y. N. Antonenko, A. Lyakhovich, I. A. Osterman, A. A. Bogdanov, and N. V. Sumbatyan. Antibiotics, 2021, 10, 489. https://doi.org/10.3390/antibiotics10050489

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. O. V. Tsepaeva, T. I. Salikhova, L. R. Grigoreva, D. V. Ponomaryov, T. Dang, R. A. Ishkaeva, T. I. Abdullin, A. V. Nemtarev, and V. F. Mironov. Med. Chem. Res., 2021, 30, 925. https://doi.org/10.1007/s00044-020-02674-6

    Article  CAS  Google Scholar 

  12. A. V. Artemev, E. A. Pritchina, M. I. Rakhmanova, N. P. Gritsan, I. Yu. Bagryanskaya, S. F. Malysheva, and N. A. Belogorlova. Dalton Trans., 2019, 48, 2328. https://doi.org/10.1039/C8DT04328K

    Article  CAS  PubMed  Google Scholar 

  13. V. V. Sharutin, O. K. Sharutina, N. M. Tarasova, and O. S. Eltsov. Russ. J. Gen. Chem., 2021, 91, 2187. https://doi.org/10.1134/S1070363221110086

    Article  CAS  Google Scholar 

  14. A. R. Zykova, V. V. Sharutin, and O. K. Sharutina. Russ. J. Inorg. Chem., 2021, 66, 56. https://doi.org/10.1134/S0036023621010149

    Article  CAS  Google Scholar 

  15. V. V. Shatutin, V. S. Senchurin, O. K. Sharutina, and E. A. Boyarkina. Russ. J. Gen. Chem., 2009, 79, 78. https://doi.org/10.1134/S1070363209010125

    Article  CAS  Google Scholar 

  16. V. V. Sharutin, O. K. Sharutina, A. V. Rybakova, and Yu. O. Gubanova. Russ J. Gen. Chem., 2018, 88, 1629. https://doi.org/10.1134/S1070363218080133

    Article  CAS  Google Scholar 

  17. V. V. Sharutin, N. Mukusheva, and A. V. Urzhumova. Vestn. Yuzhno-Ural. Gos. Univ.: Ser. Khim., 2018, 10, 48. [In Russian] https://doi.org/10.14529/chem180206

    Article  Google Scholar 

  18. V. V. Sharutin, O. K. Sharutina, and Yu. O. Gubanova. Izv. Vyssh. Uchebn. Zaved.: Khim. Khim. Tekhnol., 2019, 62(2), 4. https://doi.org/10.6060/ivkkt.20196202.5823

  19. F. Sodano, B. Rolando, F. Spyrakis, M. Failla, L. Lazzarato, E. Gazzano, C. Riganti, R. Fruttero, A. Gasco, and S. Sortino. ChemMedChem, 2018, 13, 1238. https://doi.org/10.1002/cmdc.201800088

    Article  CAS  PubMed  Google Scholar 

  20. V. F. Mironov, A. V. Nemtarev, O. V. Tsepaeva, M. N. Dimukhametov, I. A. Litvinov, A. D. Voloshina, T. N. Pashirova, E. A. Titov, A. P. Lyubina, S. K. Amerhanova, A. T. Gubaidullin, and D. R. Islamov. Molecules, 2021, 26, 6350. https://doi.org/10.3390/molecules2621635

  21. N. R. Khasiyatullina, A. T. Gubaidullin, A. M. Shinkareva, D. R. Islamov, and V. F. Mironov. Russ. Chem. Bull., Int. Ed., 2020, 69, 2140. https://doi.org/10.1007/s11172-020-3012-3

    Article  CAS  Google Scholar 

  22. S. Romanov, A. Aksunova, Y. Bakhtiyarova, M. Shulaeva, O. Pozdeev, S. Egorova, I. Galkina, and V. Galkin. J. Organomet. Chem., 2020, 910, 121130. https://doi.org/10.1016/j.jorganchem.2020.121130

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  25. H. Akutsu, J. Yamada, S. Nakatsuji, and S. S. Turner. CrystEngComm, 2009, 11, 2588. https://doi.org/10.1039/b909519e

    Article  CAS  Google Scholar 

  26. A. Onoda, Y. Yamada, M. Doi, T. Okamura, and N. Ueyama. Inorg. Chem., 2001, 40, 516. https://doi.org/10.1021/ic0003067

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. F. Camerel, G. Le Helloco, T. Guizouarn, O. Jeannin, M. Fourmigue, A. Frąckowiak, I. Olejniczak, R. Swietlik, A. Marino, E. Collet, L. Toupet, P. Auban-Senzier, and E. Canadell. Cryst. Growth Des., 2013, 13, 5135. https://doi.org/10.1021/cg401416h

    Article  CAS  Google Scholar 

  29. E. G. Ferrer, P. A. M. Williams, and E. E. Castellano. Z. Anorg. Allg. Chem., 2002, 628, 1979. https://doi.org/10.1002/1521-3749(200209)628:9/10<1979::AID-ZAAC1979>3.0.CO;2-V

    Article  CAS  Google Scholar 

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

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

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

    Article  CAS  Google Scholar 

  33. B. N. Tarasevich. IK spektry osnovnykh klassov organicheskikh soedinenii (IR Spectra of the Main Classes of Organic Compounds). Moscow: MGU, 2012. [In Russian]

  34. A. V. Vasilev, E. V. Grinenko, A. O. Schukin, and T. G. Fedulina. Infrakrasnaya spektroskopiya organicheskikh i prirodnykh soedinenii (Infrared Spectroscopy of Organic and Natural Compounds). St. Petersburg: SPbFTU, 2007. [In Russian]

  35. B. Cordero, V. Gómez, A. E. Platero-Prats, M. Revés, J. Echeverría, E. Cremades, and S. Alvarez. Dalton Trans., 2008, 21, 2832. https://doi.org/10.1039/B801115J

    Article  PubMed  Google Scholar 

  36. R. Gillespie and I. Hargittai. The VSEPR Model of Geometry. Boston: Allyn &amp;amp; Bacon, 1991.

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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. South Ural State University (National Research University), Chelyabinsk, Russia

    V. V. Sharutin, O. K. Sharutina & E. S. Mekhanoshina

Authors
  1. V. V. Sharutin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. K. Sharutina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. S. Mekhanoshina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Sharutin.

Ethics declarations

The authors declare that they have no conflicts of interests.

Additional information

Russian Text © The Author(s), 2022, published in Zhurnal Strukturnoi Khimii, 2022, Vol. 63, No. 10, 99532.https://doi.org/10.26902/JSC_id99532

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sharutin, V.V., Sharutina, O.K. & Mekhanoshina, E.S. A STUDY OF CRYSTAL STRUCTURES OF ORGANYL-TRIPHENYLPHOSPHONIUM 2,4-DINITROBENZENE SULPHONATES [Ph3PR][OSO2C6H3(NO2)2-2,4], R = CH2OMe, CH2CN, CH2CH = CHCH2PPh3. J Struct Chem 63, 1629–1638 (2022). https://doi.org/10.1134/S0022476622100092

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476622100092

Keywords

Search

Navigation