Advertisement

Russian Journal of Physical Chemistry A

, Volume 93, Issue 11, pp 2187–2191 | Cite as

Synthesis of Phosphonium Enamines: Physicochemical Properties of Dimethylsulfoxide Solutions

  • S. A. Borodkin
  • E. A. Kazoyan
  • L. D. Popov
  • G. A. Shaginyan
  • A. R. Sarkisyan
  • I. N. Shcherbakov
  • Sh. A. MarkaryanEmail author
PHYSICAL CHEMISTRY OF SOLUTIONS
  • 5 Downloads

Abstract

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.

Keywords:

enamine molar volume micelle formation 

Notes

ACKNOWLEDGMENTS

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

FUNDING

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).

REFERENCES

  1. 1.
    J. S. Modica-Napolitano and J. R. Aprille, Adv. Drug Deliv. Rev. 49, 63 (2001).CrossRefGoogle Scholar
  2. 2.
    M. P. Murphy, Biochim. Biophys. Acta 1777, 1028 (2008).CrossRefGoogle Scholar
  3. 3.
    C. M. Porteous, A. Logan, C. Evans, et al., Biochim. Biophys. Acta 1800, 1009 (2010).CrossRefGoogle Scholar
  4. 4.
    S. Le Trionnaire, A. Perry, B. Szczesny, et al., Med. Chem. Commun. 5, 728 (2014).CrossRefGoogle Scholar
  5. 5.
    M. Millard, J. D. Gallagher, B. Z. Olenyuk, and N. Neamat, J. Med. Chem. 56, 9170 (2013).CrossRefGoogle Scholar
  6. 6.
    S. Chalmers, S. T. Caldwell, C. Quin, et al., J. Am. Chem. Soc. 134, 758 (2012).CrossRefGoogle Scholar
  7. 7.
    D. A. Stoyanovsky, J. Jiang, M. P. Murphy, et al., ACS Med. Chem. Lett. 5, 1304 (2014).CrossRefGoogle Scholar
  8. 8.
    Z. W. Yu and P. J. Quinn, Biosci. Rep. 14, 259 (1994).CrossRefGoogle Scholar
  9. 9.
    S. W. Jacob and R. Herschler, Cryobiology 23, 14 (1986).CrossRefGoogle Scholar
  10. 10.
    S. A. Markarian, S. Bonora, K. A. Bagramyan, and V. B. Arakelyan, Cryobiology 49, 1 (2004).CrossRefGoogle Scholar
  11. 11.
    S. A. Markarian, A. M. Asatryan, K. R. Grigoryan, and H. R. Sargsyan, Biopolymers 82, 1 (2006).CrossRefGoogle Scholar
  12. 12.
    H. H. Ghazoyan and S. A. Markarian, J. Mol. Liq. 183, 85 (2013).CrossRefGoogle Scholar
  13. 13.
    E. A. Kazoyan, A. M. Terzyan, and Sh. A. Markaryan, Russ. J. Phys. Chem. A 85, 612 (2011).CrossRefGoogle Scholar
  14. 14.
    B. Orlich and R. Schomacker, Adv. Biochem. Eng. Biotechnol. 75, 185 (2002).PubMedGoogle Scholar
  15. 15.
    J. D. Hoefelmeyer, H. Liu, G. A. Somorjai, and T. D. Tilley, J. Colloid Interface Sci. 309, 86 (2007).CrossRefGoogle Scholar
  16. 16.
    K. I. Evstratova, N. A. Kupina, and E. E. Malakhov, Physical and Colloid Chemistry (Vysshaya Shkola, Moscow, 1990) [in Russian].Google Scholar
  17. 17.
    Sh. A. Markaryan, A. R. Sarkisyan, and G. A. Shaginyan, Russ. J. Phys. Chem. A 89, 1808 (2015).CrossRefGoogle Scholar
  18. 18.
    S. A. Borodkin, L. D. Popov, M. R. Milenković, et al., Phosphorus, Sulfur Silicon Relat. Elem. 192, 1079 (2017).CrossRefGoogle Scholar
  19. 19.
    A. A. Shvets, S. A. Borodkin, G. P. Safaryan, and V. A. Kogan, Russ. J. Gen. Chem. 72, 1346 (2002).CrossRefGoogle Scholar
  20. 20.
    S. M. C. Sousa, E. F. G. Barbosa, and I. M. S. Lampreia, J. Chem. Thermodyn. 56, 60 (2013).CrossRefGoogle Scholar
  21. 21.
    H. Kumar, K. Kaur, and S. Kumar, J. Mol. Liq. 162, 89 (2011).CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • S. A. Borodkin
    • 1
  • E. A. Kazoyan
    • 2
  • L. D. Popov
    • 1
  • G. A. Shaginyan
    • 2
  • A. R. Sarkisyan
    • 2
  • I. N. Shcherbakov
    • 1
  • Sh. A. Markaryan
    • 2
    Email author
  1. 1.Southern Federal UniversityRostov-on-DonRussia
  2. 2.Yerevan State UniversityYerevanArmenia

Personalised recommendations