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Synthesis of Phosphonium Enamines: Physicochemical Properties of Dimethylsulfoxide Solutions


Dimethylsulfoxide solutions of the products of the condensation of formylmethyl(triphenyl)phosphonium chloride with amines of different nature are studied via densitometry, elemental analysis, and IR, 1H NMR, and UV–Vis spectroscopy. Compounds containing carboxyl groups are found to be capable of forming micelles. It is concluded that the substantial drop in the molar volume as the temperature rises for a compound containing butyl radicals suggests the solution contains only one isomer at elevated temperatures.

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  1. J. S. Modica-Napolitano and J. R. Aprille, Adv. Drug Deliv. Rev. 49, 63 (2001).

    CAS  Article  Google Scholar 

  2. M. P. Murphy, Biochim. Biophys. Acta 1777, 1028 (2008).

    CAS  Article  Google Scholar 

  3. C. M. Porteous, A. Logan, C. Evans, et al., Biochim. Biophys. Acta 1800, 1009 (2010).

    CAS  Article  Google Scholar 

  4. S. Le Trionnaire, A. Perry, B. Szczesny, et al., Med. Chem. Commun. 5, 728 (2014).

    CAS  Article  Google Scholar 

  5. M. Millard, J. D. Gallagher, B. Z. Olenyuk, and N. Neamat, J. Med. Chem. 56, 9170 (2013).

    CAS  Article  Google Scholar 

  6. S. Chalmers, S. T. Caldwell, C. Quin, et al., J. Am. Chem. Soc. 134, 758 (2012).

    CAS  Article  Google Scholar 

  7. D. A. Stoyanovsky, J. Jiang, M. P. Murphy, et al., ACS Med. Chem. Lett. 5, 1304 (2014).

    CAS  Article  Google Scholar 

  8. Z. W. Yu and P. J. Quinn, Biosci. Rep. 14, 259 (1994).

    CAS  Article  Google Scholar 

  9. S. W. Jacob and R. Herschler, Cryobiology 23, 14 (1986).

    CAS  Article  Google Scholar 

  10. S. A. Markarian, S. Bonora, K. A. Bagramyan, and V. B. Arakelyan, Cryobiology 49, 1 (2004).

    CAS  Article  Google Scholar 

  11. S. A. Markarian, A. M. Asatryan, K. R. Grigoryan, and H. R. Sargsyan, Biopolymers 82, 1 (2006).

    CAS  Article  Google Scholar 

  12. H. H. Ghazoyan and S. A. Markarian, J. Mol. Liq. 183, 85 (2013).

    CAS  Article  Google Scholar 

  13. E. A. Kazoyan, A. M. Terzyan, and Sh. A. Markaryan, Russ. J. Phys. Chem. A 85, 612 (2011).

    CAS  Article  Google Scholar 

  14. B. Orlich and R. Schomacker, Adv. Biochem. Eng. Biotechnol. 75, 185 (2002).

    CAS  PubMed  Google Scholar 

  15. J. D. Hoefelmeyer, H. Liu, G. A. Somorjai, and T. D. Tilley, J. Colloid Interface Sci. 309, 86 (2007).

    CAS  Article  Google Scholar 

  16. K. I. Evstratova, N. A. Kupina, and E. E. Malakhov, Physical and Colloid Chemistry (Vysshaya Shkola, Moscow, 1990) [in Russian].

    Google Scholar 

  17. Sh. A. Markaryan, A. R. Sarkisyan, and G. A. Shaginyan, Russ. J. Phys. Chem. A 89, 1808 (2015).

    CAS  Article  Google Scholar 

  18. S. A. Borodkin, L. D. Popov, M. R. Milenković, et al., Phosphorus, Sulfur Silicon Relat. Elem. 192, 1079 (2017).

    CAS  Article  Google Scholar 

  19. A. A. Shvets, S. A. Borodkin, G. P. Safaryan, and V. A. Kogan, Russ. J. Gen. Chem. 72, 1346 (2002).

    CAS  Article  Google Scholar 

  20. S. M. C. Sousa, E. F. G. Barbosa, and I. M. S. Lampreia, J. Chem. Thermodyn. 56, 60 (2013).

    CAS  Article  Google Scholar 

  21. H. Kumar, K. Kaur, and S. Kumar, J. Mol. Liq. 162, 89 (2011).

    CAS  Article  Google Scholar 

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This work was performed on equipment at the Molecular Spectroscopy Center of Southern Federal University’s shared scientific resource center.


This work was supported by Southern Federal University; the State Committee for Science, Ministry of Education and Science of the Republic of Armenia; and Yerevan State University, Republic of Armenia (joint scientific project no. VnGr-07/2017-35).

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Correspondence to Sh. A. Markaryan.

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Translated by V. Glyanchenko

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Borodkin, S.A., Kazoyan, E.A., Popov, L.D. et al. Synthesis of Phosphonium Enamines: Physicochemical Properties of Dimethylsulfoxide Solutions. Russ. J. Phys. Chem. 93, 2187–2191 (2019).

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  • enamine
  • molar volume
  • micelle formation