Alkyltriphenylphosphonium Arenesulfonates: Synthesis and Structures

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

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).

全文:

受限制的访问

作者简介

V. Sharutin

South Ural State University (National Research University)

编辑信件的主要联系方式.
Email: sharutin50@mail.ru
俄罗斯联邦, Chelyabinsk

O. Sharutina

South Ural State University (National Research University)

Email: sharutin50@mail.ru
俄罗斯联邦, Chelyabinsk

E. Mekhanoshina

South Ural State University (National Research University)

Email: sharutin50@mail.ru
俄罗斯联邦, Chelyabinsk

参考

  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.

补充文件

附件文件
动作
1. JATS XML
下载
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)°.

下载 (104KB)
索引源数据
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)°.

下载 (100KB)
索引源数据
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)°.

下载 (89KB)
索引源数据
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)°.

下载 (80KB)
索引源数据
6. Fig. 5. The chain of arenesulfonate anions in crystal I.

下载 (71KB)
索引源数据

版权所有 © Российская академия наук, 2024