Advertisement

Russian Chemical Bulletin

, Volume 65, Issue 7, pp 1761–1772 | Cite as

Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity

  • S. Z. Vatsadze
  • G. V. Gavrilova
  • F. S. Zyuz’kevich
  • V. N. Nuriev
  • D. P. Krut’ko
  • A. A. Moiseeva
  • A. V. Shumyantsev
  • A. I. Vedernikov
  • A. V. Churakov
  • L. G. Kuz’mina
  • J. A. K. Howard
  • S. P. Gromov
Full Articles

Abstract

A series of cross-conjugated dienones was synthesized to study the dependence of physicochemical characteristics on the nature of substituents in the aromatic groups of symmetric cyclopentanone dibenzylidene derivatives. The structure of compounds was established by electronic, IR, and NMR spectroscopy and X-ray diffraction study. All the compounds obtained possess the E,E-geometry. In the crystalline state, the arrangement of the dienone molecules is unfavorable for the intermolecular [2+2] photocycloaddition to take place. The low-temperature phases transition for unsubstituted diphenyl derivative of cyclopentanone was detected using variable-temperature X-ray diffraction and differential scanning calorimetry. Oxidation and reduction potentials of the dienones were measured by cyclic voltammetry. Their dependence on the nature and placement of substituents in the benzene rings was demonstrated. A linear correlation (R = 0.9343) between the difference of electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum was found, that allows us to recommend the use of the data obtained in the correlation analysis of other compounds of this class.

Keywords

dienones synthesis NMR spectroscopy X-ray diffraction differential scanning calorimetry supramolecular chemistry [2+2] photocycloaddition CVA electronic spectroscopy correlation analysis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    V. P. Ananikov, L. L. Khemchyan, Yu. V. Ivanova, V. I. Bukhtiyarov, A. M. Sorokin, I. P. Prosvirin, S. Z. Vatsadze, A. V. Medved’ko, V. N. Nuriev, A. D. Dilman, V. V. Levin, I. P. Koptyug, K. V. Kovtunov, V. V. Zhivonitko, V. A. Likholobov, A. V. Romanenko, P. A. Simonov, V. G. Nenajdenko, O. I. Shmatova, V. M. Muzalevskiy, M. S. Nechaev, A. F. Asachenko, O. S. Morozov, P. B. Dzhevakov, S. N. Osipov, D. V. Vorobyeva, M. A. Topchiy, M. A. Zotova, S. A. Ponomarenko, O. V. Borshchev, Yu. N. Luponosov, A. A. Rempel, A. A. Valeeva, A. Yu. Stakheev, O. V. Turova, I. S. Mashkovsky, S. V. Sysolyatin, V. V. Malykhin, G. A. Bukhtiyarova, A. O. Terent’ev, I. B. Krylov, Russ. Chem. Rev., 2014, 83, 885.CrossRefGoogle Scholar
  2. 2.
    Organic Reactions, vol. 10, Ed. R. Adams, Wiley, 1959, 576.Google Scholar
  3. 3.
    S. Z. Vatsadze, A. G. Golikov, A. P. Kriven’ko, N. V. Zyk, Russ. Chem. Rev., 2008, 77, 661.CrossRefGoogle Scholar
  4. 4.
    J. Cui, D. Crich, D. Wink, M. Lam, A.L. Rheingold, D. A. Case, W. T. Fu, Y. Zhou, M. Rao, A. J. Olson, M. E. Johnson, Bioorg. Med. Chem., 2003, 11, 3379.CrossRefGoogle Scholar
  5. 5.
    M. M. Gar, O. N. Arkhipova, S. V. Popkov, Agrokhimiya [Agrochemistry], 2009, 6, 40 (in Russian).Google Scholar
  6. 6.
    U. Cersosimo, A. Sgorbissa, C. Foti, S. Drioli, R. Angelica, A. Tomasella, R. Picco, M. S. Semrau, P. Storici, F. Benedetti, F. Berti, C. Brancolini, J. Med. Chem., 2015, 58, 1691.Google Scholar
  7. 7.
    S. Z. Vatsadze, M. A. Kovalkina, N. V. Sviridenkova, N. V. Zyk, A. V. Churakov, L. G. Kuz’mina, J. A. K. Howard, CrystEngComm, 2004, 6, 112.CrossRefGoogle Scholar
  8. 8.
    S. Z. Vatsadze, I. A. Vatsadze, M. A. Manaenkova, N. V. Zyk, A. V. Churakov, M. Yu. Antipin, J. A. K. Howard, H. Lang, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 1775 [Izv. Akad. Nauk, Ser. Khim., 2007, 1712].CrossRefGoogle Scholar
  9. 9.
    A. A. M. Aly, S. Z. Vatsadze, A. V. Chernikov, B. Walfort, T. Rüffer, H. Lang, Polyhedron, 2007, 26, 3925.CrossRefGoogle Scholar
  10. 10.
    E. M. Sanford, K. W. Paulisse, J. T. Reeves, J. Appl. Polym. Sci., 1999, 74, 2255.CrossRefGoogle Scholar
  11. 11.
    A. Grandeury, S. Petit, S. Coste, G. Coquerel, C. Perrio, G. Gouhier, Chem. Commun., 2005, 4007.Google Scholar
  12. 12.
    S. Z. Vatsadze, M. A. Manaenkova, N. V. Sviridenkova, N. V. Zyk, D. P. Krut’ko, A. V. Churakov, M. Yu. Antipin, J. A. K. Howard, H. Lang, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 1184 [Izv. Akad. Nauk, Ser. Khim., 2006, 1141].CrossRefGoogle Scholar
  13. 13.
    Z. Aizenshtat, M. Hausman, Y. Pickholtz, D. Tal, J. Blum, J. Org. Chem., 1977, 42, 2386.CrossRefGoogle Scholar
  14. 14.
    H. George, H. J. Roth, Tetrahedron Lett., 1971, 12, 4057.CrossRefGoogle Scholar
  15. 15.
    G. Kaupp, I. Zimmerman, Angew. Chem., 1981, 83, 1107.CrossRefGoogle Scholar
  16. 16.
    I. G. Ovchinnikova, D. K. Nikulov, E. V. Bartashevich, E. G. Matochkina, M. I. Kodess, P. A. Slepukhin, A. V. Druzhinin, O. V. Fedorova, G. L. Rusinov, V. N. Charushin, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 824 [Izv. Akad. Nauk, Ser. Khim., 2011, 805].CrossRefGoogle Scholar
  17. 17.
    L. G. Kuz’mina, A. I. Vedernikov, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, CrystEngComm, 2015, 17, 4584.CrossRefGoogle Scholar
  18. 18.
    S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz’mina, S. N. Dmitrieva, Yu. A. Strelenko, J. A. K. Howard, J. Org. Chem., 2014, 79, 11416.CrossRefGoogle Scholar
  19. 19.
    M. V. Alfimov, S. P. Gromov, O. B. Stanislavskii, E. N. Ushakov, O. A. Fedorova, Russ. Chem. Bull. (Int. Ed.), 1993, 42, 1385 [Izv. Akad. Nauk, Ser. Khim., 1993, 1449].CrossRefGoogle Scholar
  20. 20.
    K. Biradha, R. Santra, Chem. Soc. Rev., 2013, 42, 950.CrossRefGoogle Scholar
  21. 21.
    R. Santra, M. Garai, D. Mondal, K. Biradha, Chem. Eur. J., 2013, 19, 489.CrossRefGoogle Scholar
  22. 22.
    E. Elacqua, P. Kaushik, R. H. Groeneman, J. C. Sumrak, D.-K. Bu ar, L. R. MacGillivray, Angew. Chem. (Int. Ed.), 2012, 51, 1037.CrossRefGoogle Scholar
  23. 23.
    R. Santra, K. Biradha, CrystEngComm, 2011, 13, 3246.CrossRefGoogle Scholar
  24. 24.
    V. N. Nuriev, F. S. Zyuz’kevich, S. Z. Vatsadze, A. I. Vedernikov, S. P. Gromov, Pat. RF No. 2568614; Byul. isobret. [Invention Bull.], 2015, No. 32 (in Rusian).Google Scholar
  25. 25.
    S. V. Tsukerman, L. A. Kutulya, V. F. Lavrushin, Russ. J. Org. Chem. (Engl. Transl.), 1964, 34, 3597 [Zh. Org. Khim., 1964, 34, 3597].Google Scholar
  26. 26.
    R. M. Issa, S. H. Etaiw, I. M. Issa, A. K. El-Shafie, Acta Chim. Acad. Sceint. Hung., 1976, 89, 381.Google Scholar
  27. 27.
    C. R. Theocharis, W. Jones, J. M. Thomas, M. Motevalli, M. B. Hursthouse, J. Chem. Soc., Perkin Trans. 2, 1984, 71.Google Scholar
  28. 28.
    J. Kawamata, K. Inoue, T. Inabe, Bull. Chem. Soc. Jpn, 1998, 71, 2777.CrossRefGoogle Scholar
  29. 29.
    R. J. Butcher, J. P. Jasinski, B. Narayana, B. K. Sarojini, S. Bindya, H. S. Yathirajan, Acta Crystallogr., Sect. E, 2007, 63, o3270.CrossRefGoogle Scholar
  30. 30.
    G. J. M. Schmidt, J. Pure Appl. Chem., 1971, 27, 647.Google Scholar
  31. 31.
    E. K. Beloglazkina, I. V. Yudin, A. G. Mazhuga, A. A. Moiseeva, S. V. Zatonskii, N. V. Zyk, Russ. Chem. Bull. (Int. Ed.), 2008, 57, 577 [Izv. Akad. Nauk, Ser. Khim., 2008, 565].CrossRefGoogle Scholar
  32. 32.
    Organic Electrochemistry. An Introduction and a Guide, Eds M. M. Baizer, H. Lund, Marcel Dekker, New York, 1983.Google Scholar
  33. 33.
    J. A. Morales-Morales, C. Frontana, M. Aguilar-Martýnez, J. A. Bautista-Martýnez, F. J. Gonzalez, I. Gonzalez, J. Phys. Chem. A, 2007, 111, 8993.CrossRefGoogle Scholar
  34. 34.
    F. J. Arévalo, P. G. Molina, M. A. Zn, H. Fernández, J. Electroanal. Chem., 2008, 619–20, 46.CrossRefGoogle Scholar
  35. 35.
    A. G. Majouga, E. K. Beloglazkina, A. A. Moiseeva, O. V. Shilova, E. A. Manzheliy, M. A. Lebedeva, D. E. Stephen, A. N. Khlobystov, N. V. Zyk, Dalton Trans., 2013, 6290.Google Scholar
  36. 36.
    G. V. Zakharova, F. S. Zyuz’kevich, V. N. Nuriev, S. Z. Vatsadze, V. G. Plotnikov, S. P. Gromov, High Energy Chem. (Engl. Transl.), 2016, 50, 27 [Khim. Vysokikh Energii, 2016, 50, 29].CrossRefGoogle Scholar
  37. 37.
    M. Al-Anber, S. Vatsadze, R. Holze, H. Lang, W. R. Thiel, Dalton Trans., 2005, 3632.Google Scholar
  38. 38.
    S. Vatsadze, M. Al-Anber, W. R. Thiel, H. Lang, R. Holze, J. Solid State Electrochem., 2005, 9, 764.CrossRefGoogle Scholar
  39. 39.
    Spartan’ 14, version 1.2.0 for Mac, Wavefunction Inc.Google Scholar
  40. 40.
    G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, 64, 112.CrossRefGoogle Scholar
  41. 41.
    G. M. Sheldrick, SADABS, Program for Scaling and Correction of Area Detector Data, University of Göttingen, Germany, 1997.Google Scholar
  42. 42.
    C. Zhao, S. Yang, Y. Cai, X. Li, X. He, W. Li, G. Liang, J. Li, Eur. J. Med. Chem., 2010, 45, 5773.CrossRefGoogle Scholar
  43. 43.
    Z. Li, N. Pucher, K. Cicha, J. Torgersen, S. C. Ligon, A. Ajami, W. Husinsky, A. Stampfl, R. Liska, Macromolecules, 2013, 46, 352.CrossRefGoogle Scholar
  44. 44.
    Z.-Y. Du, R.-R. Liu, W.-Y. Shao, Z.-S. Huang, X.-P. Mao, A. S. C. Chain, L. Ma, L.-Q. Gu, Eur. J. Med. Chem., 2006, 41, 213.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • S. Z. Vatsadze
    • 1
  • G. V. Gavrilova
    • 1
  • F. S. Zyuz’kevich
    • 2
  • V. N. Nuriev
    • 1
  • D. P. Krut’ko
    • 1
  • A. A. Moiseeva
    • 1
  • A. V. Shumyantsev
    • 1
  • A. I. Vedernikov
    • 2
  • A. V. Churakov
    • 3
  • L. G. Kuz’mina
    • 3
  • J. A. K. Howard
    • 4
  • S. P. Gromov
    • 1
    • 2
  1. 1.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscowRussian Federation
  2. 2.Center of PhotochemistryRussian Academy of SciencesMoscowRussian Federation
  3. 3.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  4. 4.Chemistry DepartmentDurham UniversityDurhamUK

Personalised recommendations