Skip to main content
Log in

Structure and Ion-Selective Properties of 2-Phosphorylphenols

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The structure and ion-selective properties of some 2-phosphorylphenols were studied. It was shown that, irrespective of the nature of the substituents on the benzene ring and on the phosphorus atom, these compounds exhibit potentiometric selectivity to cesium cation. The crystal structures of 2-(diphenylphosphoryl)-4-ethylphenol and 2-[(diphenylphosphoryl)methyl]phenol were established.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Bondarenko, N.A., Tsvetkov, E.N., Matrosov, E.I., and Kabachnik, M.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1979, no. 2, p. 432.

    Google Scholar 

  2. Henning, H.G. and Wild, W., J. Prakt. Chem., 1976, vol. 318, no. 1, p. 69.

    Article  CAS  Google Scholar 

  3. Shvets, A.A., Popov, L.D., Kogan, V.A., Litvinov, V.V., and Etmetchenko, L.N., Zh. Obshch. Khim., 1988, vol. 58, p. 1046.

    CAS  Google Scholar 

  4. Baulin, V.E., Doctoral (Chem.) Dissertation, Chernogolovka, 2012.

    Google Scholar 

  5. Petrukhin, O.M., Shipulo, E.V., Krylova, S.A., Rogatinskaya, S.L., Zhukov, A.F., Wilke, S., Müller, H., Tsvetkov, E.N., Baulin, V.E., Syundyukova, V.Kh., and Bondarenko, N.A., Zh. Anal. Khim., 1994, vol. 49, no. 12, p. 1299.

    CAS  Google Scholar 

  6. Krivorot’ko, E.S., Polyakova, I.N., Ivanova, I.S., Pyatova, E.N., Baulin, V.E., Galkina, E.N., Dorokhov, A.V., and Tsivadze A.Yu., Russ. J. Inorg. Chem., 2016, vol. 61, p. 1241. doi 10.1134/S0036023616100132

    Article  CAS  Google Scholar 

  7. Petrukhin, O.M., Kurachenkova, S.N., Sonina, E.A., Shipulo, E.V., and Baulin, V.E., J. Anal. Chem., 2002, vol. 57, no. 3, p. 264. doi 10.1023/A:1014408818914

    Article  CAS  Google Scholar 

  8. Petrukhin, O.M., Frakisky, Ye.V., Kharitonov, A.B., Urusov, Yu.I., and Baulin, V.Ye., Anal. Chim. Acta, 1999, vol. 385, p. 125.

    CAS  Google Scholar 

  9. RF Patent 2054666, 1996.

  10. Ivanova, I.S., Polyakova, I.N., Krivorot’ko, E.S., Pyatova, E.N., Baulin, V.E., and Tsivadze, A.Yu., Russ. J. Inorg. Chem., 2017, vol. 62, no. 10, p. 1299. doi 10.1134/S0036023617100102

    Article  CAS  Google Scholar 

  11. Pyatova, E.N., Polyakova, I.N., Ivanova, I.S., Krivorot’ko, E.S., Galkina, E.N., Baulin, V.E., and Tsivadze, A.Yu., Russ. J. Inorg. Chem., 2017, vol. 62, no. 4, p. 431. doi 10.1134/S0036023617040143

    Article  CAS  Google Scholar 

  12. Petrukhin, O.M., Evsevleeva, L.G., Urusov, Yu.I., Borzhitskii, Yu.A., Tsvetkov, E.N., Baulin, V.E., Syundyukova, V.Kh., and Bondarenko, N.A., Zh. Anal. Khim., 1995, vol. 50, no. 1, p. 60.

    Google Scholar 

  13. Garifzyanov, A.R., Khramov, A.N., and Toropova, V.F., Zh. Anal. Khim., 1991, vol. 46, no. 1, p. 133.

    CAS  Google Scholar 

  14. Mistlberger, G., Crespo, G.A., and Bakker, E., Annu. Rev. Anal. Chem., 2014, vol. 7, p. 483. doi 10.1146/annurev-anchem-071213-020307

    Article  CAS  Google Scholar 

  15. Buhlmann, P. and Chen, L.D., Ion-Selective Electrodes with Ionophore-Doped Sensing Membranes in Supramolecular Chemistry: From Molecules to Nanomaterials, Minneapolis: Wiley, 2012. doi 10.1002/9780470661345.smc097

    Google Scholar 

  16. Bakker, E. and Meir, A.J., SIAM Review, 2003, vol. 45, no. 2, p. 327.

    Article  Google Scholar 

  17. Bakker, Е., Buhlmann, P., and Pretsch, Е., Chem. Rev., 1997, vol. 97, p. 3083. doi 10.1021/cr940394a

    Article  CAS  PubMed  Google Scholar 

  18. Pechenkina, I.A. and Mikhelson, K.N., Russ. J. Electrochem., 2015, vоl. 51, no. 2, p. 93. doi 10.1134/S1023193515020111

    Google Scholar 

  19. Mikhelson, K.N., J. Anal. Chem., 2012, vol. 67, no. 1, p. 4. doi 10.1134/S1061934811110104

    Article  CAS  Google Scholar 

  20. Shuvaev, S., Kotova, O., Utochnikova, V., Vaschenko, A., Puntus, L., Baulin, V., Kuzmina, N., and Tzivadze, A., Inorg. Chem. Commun., 2012, vol. 20, p. 73. doi 10.1016/j.inoche.2012.02.020

    Article  CAS  Google Scholar 

  21. Matveeva, A.G., Starikova, Z.A., Matrosov, E.I., Bodrin, G.V., Matveev, S.V., and Nifant’ev, E.E., Russ. J. Inorg. Chem., 2006, vol. 51, no. 2, p. 253. doi 10.1134/S0036023606020136

    Article  Google Scholar 

  22. Shuvaev, S., Bushmarinov, I.S., Sinev, I., Dmitrienko, A.O., Lyssenko, K.A., Baulin, V., Grünert, W., Tsivadze, A.Yu., and Kuzmina, N., Eur. J. Inorg. Chem., 2013, vol. 2013, no. 27, p. 4823. doi 10.1002/ejic.201300540

    Article  CAS  Google Scholar 

  23. Qi, N., Zhang, N., Allu, S.R., Gao, J., Guo, J., and He, Y., Org. Lett., 2016, vol. 18, p. 6204. doi 10.1021/acs.orglett.6b03283

    Article  CAS  PubMed  Google Scholar 

  24. Belanger-Gariepy, F., Dartiguenave, M., Loiseau, F., and Beauchamp, A.L., Acta Crystallogr., Sect. C, 2000, vol. 56, p. 338. doi 10.1107/S0108270100008878

    Article  Google Scholar 

  25. Hein, P., Lugger, T., Hahn, F.E., Rettig, S.J., and Orvig, C., Z. Kristallogr.–New Cryst. Struct., 2000, vol. 215, p. 237. doi 10.1515/ncrs-2000-0223

    CAS  Google Scholar 

  26. Tkachev, V.V. and Atovmyan, L.O., Zh. Strukt. Khim., 1993, vol. 34, no. 3, p. 109.

    CAS  Google Scholar 

  27. Nelubina, Y.V., Alexanyan, D.V., Kozlov, V.A., Lyssenko, K.A., and Odinets, I.L., Acta Crystallogr., Sect. E, 2005, vol. 61, p. o2539. doi 10.1107/S1600536805021811

  28. Groom, C.R. and Allen, F.H., Angew. Chem. Int. Ed., 2014, vol. 53, p. 662. doi 10.1002/anie.201306438

    Article  CAS  Google Scholar 

  29. Matveeva, A.G., Starikova, Z.A., Matrosov, E.I., Bodrin, G.V., Matveev, S.V., and Nifant’ev, E.E., Russ. J. Inorg. Chem., 2006, vol. 51, no. 2, p. 253. doi 10.1134/S0036023606020136

    Article  Google Scholar 

  30. Fallon, M.G., Mulcahy, D., Mutphy, W.S., and Glennon, J.D., Analyst, 1996, vol. 121, p. 127. doi 10.1039/AN99621FX025

    Article  CAS  Google Scholar 

  31. Bocchi, C., Careri, M., Casnati, A., and Mori, G., Anal. Chem., 1995, vol. 67, p. 4234. doi 10.1021/ac00119a005

    Article  CAS  Google Scholar 

  32. Buhlmann, P., Pretsch, E., and Bakker, E., Chem. Rev., 1998, vol. 98, no. 4, p. 1593. doi 10.1021/cr970113

    Article  PubMed  Google Scholar 

  33. Nemilova, M.Y., Shvedene, N.V., Kovalev, V.V., and Shokova, E.A., J. Anal. Chem., 2003, vol. 58, p. 375. doi 10.1023/A:1023210101450

    Article  CAS  Google Scholar 

  34. Tsvetkov, E.N., Syundyukova, V.Kh., and Baulin, V.E., Zh. Anal. Khim., 1987, vol. 57, no. 11, p. 2456.

    CAS  Google Scholar 

  35. Baulin, V.E., Syundyukova, V.Kh., and Tsvetkov, E.N., Zh. Obshch. Khim., 1989, vol. 59, no. 1, p. 62.

    CAS  Google Scholar 

  36. Evreinov, V.I., Baulin, V.E., Vostroknutova, Z.N., Bondarenko, N.A., Syundyukova, V.Kh., and Tsvetkov, E.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, no. 9, p. 1990.

    Google Scholar 

  37. Alberts, A.H., TimmLer, K., Noltes, J.G., and Spek, K., J. Am. Chem. Soc., 1979, vol. 101, p. 3376. doi 10.1021/ja00506a041

    Article  Google Scholar 

  38. Materova, E.A., Grekovich, A.L., and Didina, S.U., Elektrokhimiya, 1972, vol. 8, no. 8, pp. 1829.

    CAS  Google Scholar 

  39. IUPAC. Recommendations for Nomenclature of Ion-Selective Electrodes, Pure Appl. Chem., 1976, vol. 48, no. 1, p. 127. doi 10.1351/pac197648010127

    Article  Google Scholar 

  40. Bakker, E., Pretsch, E., and Buhlmann, P., Anal. Chem., 2000, vol. 72, p. 1127. doi 10.1021/ac991146n

    Article  CAS  PubMed  Google Scholar 

  41. APEX II and SAINT, Madison (US): Bruker AXS, 2007.

  42. Sheldrick, G.M., SADABS, Göttingen (Germany): Univ. of Göttingen, 1997.

    Google Scholar 

  43. Evans, P.R., Acta Crystallogr., Sect. D, 2006, vol. 62, p. 72. doi 10.1107/S0907444905036693

    Article  CAS  Google Scholar 

  44. Battye, T.G.G., Kontogiannis, L., Johnson, O., Powell, H.R., and Leslie, A.G.W., Acta Crystallogr., Sect. D, 2011, vol. 67, p. 271. doi 10.1107/S0907444910048675

    Article  CAS  Google Scholar 

  45. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. doi 10.1107/S2053229614024218

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. E. Baulin.

Additional information

Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © I.S. Ivanova, V.E. Baulin, E.N. Pyatova, A.B. Ilyukhin, E.N. Galkina, I.A. Yakushev, P.V. Dorovatovskii, A.Yu. Tsivadze, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1524–1531.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ivanova, I.S., Baulin, V.E., Pyatova, E.N. et al. Structure and Ion-Selective Properties of 2-Phosphorylphenols. Russ J Gen Chem 88, 1867–1873 (2018). https://doi.org/10.1134/S1070363218090177

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218090177

Keywords

Navigation