Alkyltriphenylphosphonium Arenesulfonates: Synthesis and Structures

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

The reactions of equimolar amounts of alkyltriphenylphosphonium bromide with arenesulfonic acids in an aqueous-acetone solution afford alkyltriphenylphosphonium arenesulfonates [Ph3PCH2ОMe][OSO2C6H3(OH-4)(COOH-3)] (I), [Ph3PCH2СN][OSO2C6H4(COOH)-2] (II), [Ph3PCH2C(O)Me][OSO2С6H4(COOH-2] (III), and [Ph3PCH2C(O)Me][OSO2Naft-1] (IV). According to the X-ray diffraction (XRD) data, the crystals of compounds I−IV have ionic structures with tetrahedral alkyltriphenylphosphonium cations (P−С 1.7820(19)−1.8330(20) A, CPC 05.37(10)°−112.09(12)°) and arenesulfonate anions. The crystal of compound I contains hydrogen bonds (S=O∙∙∙H−OC(O) 1.87 A) linking the arenesulfonate anions into chains. The structural organization of the crystals of compounds I−IV is mainly formed due to numerous weak hydrogen bonds between the cations and anions, for instance, S=O∙∙∙H−Car (2.29−2.70 A), C=O∙∙∙H–C (2.48 and 2.59 A), and N∙∙∙H–C (2.62−2.68 A).

Texto integral

Acesso é fechado

Sobre autores

V. Sharutin

South Ural State University (National Research University)

Autor responsável pela correspondência
Email: sharutin50@mail.ru
Rússia, Chelyabinsk

O. Sharutina

South Ural State University (National Research University)

Email: sharutin50@mail.ru
Rússia, Chelyabinsk

E. Mekhanoshina

South Ural State University (National Research University)

Email: sharutin50@mail.ru
Rússia, Chelyabinsk

Bibliografia

  1. The Chemistry of Organophosphorus Compounds, Hartley, F.R., Ed., New York: Wiley, 1983, vol. 3.
  2. Moritz, R., Wagner, M., Schollmeyer, D., et al., Chem.-Eur. J., 2015, vol. 21, p. 9119. https://doi.org/10.1002/chem.201406370
  3. Werner, T., Adv. Synth. Catal., 2009, vol. 351, p. 1469. https://doi.org/10.1002/adsc.200900211
  4. Cordovilla, C., Bartolome, C., Martinez-Ilarduya, J.M., et al., ACS Catal., 2015, vol. 5, p. 3040. https://doi.org/10.1021/acscatal.5b00448
  5. Chong, C.C., Hirao, H., and Kinjo, R., Angew. Chem., Int. Ed. Engl., 2015, vol. 127, p. 192. https://doi.org/10.1002/ange.201408760
  6. Luiz, J.F. and Spikes, H., Tribology Lett., 2020, vol. 68, p. 75. https://doi.org/10.1007/s11249-020-01315-8
  7. Zhu, Ch.-L., Zhang, F.-G., Meng, W., et al., Angew. Chem., Int. Ed. Engl., 2011, vol. 50, p. 5869. https://doi.org/10.1002/anie.201100283
  8. Cassity, C.G., Mirjafari, A., Mobarrez, N., et al., Chem. Commun., 2013, vol. 49, no. 69, p. 7590. https://doi.org/10.1039/c3cc44118k
  9. Canac, Y., Duhayon, C., and Chauvin, R., Angew. Chem., Int. Ed. Engl., 2007, vol. 46, p. 6313. https://doi.org/10.1002/anie.200701490
  10. Milenkovic, M., Warzajtis, B., Rychlewska, U., et al., Molecules, 2012, vol. 17, no. 3, p. 2567. https://doi.org/10.3390/molecules17032567
  11. Pavlova, J.A., Khairullina, Z.Z., Tereshchenkov, A.G., et al., Antibiotics, 2021, vol. 10, p. 489. https://doi.org/10.3390/antibiotics10050489
  12. Tsepaeva, O.V., Salikhova, T.I., Grigor′eva, L.R., et al., Med. Chem. Res., 2021, vol. 30, p. 925. https://doi.org/10.1007/s00044-020-02674-6
  13. Sodano, F., Rolando, B., Spyrakis, F., et al., ChemMedChem, 2018, vol. 13, p. 1238. https://doi.org/10.1002/cmdc.201800088
  14. Mironov, V.F., Nemtarev, A.V., Tsepaeva, O.V., et al., Molecules, 2021, vol. 26, p. 6350. https://doi.org/10.3390/molecules26216350
  15. Khasiyatullina, N.R., Gubaidullin, A.T., Shinkareva, A.M., et al., Russ. Chem. Bull., 2020, vol. 69, p. 2140. https://doi.org/10.1007/s11172-020-3012-3
  16. Romanov, S., Aksunova, A., Bakhtiyarova, Y., et al., J. Organomet. Chem., 2020, vol. 910, p. 121130. https://doi.org/10.1016/j.jorganchem.2020.121130
  17. Sharutin, V.V., Sharutina, O.K., and Mekhanoshina, E.S., Vest. YuUrGU. Ser. Khim., 2022, vol. 14, no. 2, p. 41.
  18. Sharutin, V.V., Sharutina, O.K., and Mekhanoshina, E.S., Russ. J. Gen. Chem., 2022, vol. 92, no. 6, p. 969.
  19. Sharutin, V.V., Sharutina, O.K., and Mekhanoshina, E.S., J. Struct. Chem., 2022, vol. 63, no. 10, p. 1629.
  20. Mekhanoshina, E.S., Vest. YuUrGU. Ser. Khim., 2023, vol. 15, no. 1, p. 31.
  21. Mekhanoshina, E.S., Vest. YuUrGU. Ser. Khim., 2023, vol. 15, no. 2, p. 55.
  22. Bruker. SMART and SAINT-Plus. Versions 5.0. Data Collection and Processing Software for the SMART System, Madison: Bruker AXS Inc., 1998.
  23. Bruker. SHELXTL/PC. Versions 5.10. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, Madison: Bruker AXS Inc., 1998.
  24. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., et al., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
  25. Tarasevich, B.N., IK-spektry osnovnykh klassov organicheskikh soedinenii (IR Spectra of Main Classses of Organic Compounds), Tarasevich, B.N., Ed., Moscow: MGU, 2012.
  26. Infrakrasnaya spektroskopiya organicheskikh i prirodnykh soedinenii: ucheb. posobie (Infrared Spectroscopy of Organic and Natural Compounds. Study Guide), Vasil′ev, A.V., Grinenko, E.V., Shchukin, A.O., et al., Eds., St.-Petersburg: SPbGLTA, 2007.

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Fig. 1. General view of connection I. Bond lengths: P—C — 1.790(2)-1.820(3); S—O — 1.443(3)-1.464(2); S—C — 1.783(2) Å and valence angles: CPC — 105.37(10)-112.09(12)°.

Baixar (104KB)
Metadados
3. Fig. 2. General view of the connection II. Bond lengths: P—C — 1.785(2)-1.833(2); S—O — 1.446(2)-1.464(2); S—C — 1.794(2) Å and valence angles: CPC — 108.31(11)-112.09(10)°.

Baixar (100KB)
Metadados
4. Fig. 3. General view of the connection III. Bond lengths: P—C — 1.784(5)-1.795(5); S—O — 1.433(4)-1.457(5); S—C — 1.786(5) Å and valence angles: CPC — 107.1(3)-112.6(3)°.

Baixar (89KB)
Metadados
5. Fig. 4. General view of the connection IV. Bond lengths: P—C — 1.782(2)-1.796(2); S—O — 1.433(2)-1.440(2) Å; S—C — 1.776(2) Å and valence angles: CPC — 105.23(9)-112.20(9)°.

Baixar (80KB)
Metadados
6. Fig. 5. The chain of arenesulfonate anions in crystal I.

Baixar (71KB)
Metadados

Declaração de direitos autorais © Российская академия наук, 2024