Russian Chemical Bulletin

, Volume 48, Issue 4, pp 734–738 | Cite as

Effect of the solvent nature and the number of electrophilic substituents in the molecule on hydration of nitro derivatives of phenanthrene-9,10-quinone

  • R. V. Linko
  • V. A. Soldatkina
  • B. E. Zaitsev
  • V. I. Sokol
  • V. V. Davydov
Organic Chemistry
  • 31 Downloads

Abstract

Solvates (1⩺2) of 10,10-dihydroxy-2,4,7-trinitro-9,10-dihydrophenanthren-9-one with DMSO and of 10,10-dihydroxy-2,7-dinitro-9,10-dihydrophenanthren-9-one with HMPA were prepared. The crystal structure of 2,5-dinitrophenanthrene-9,10-quinone was established. The results of X-ray diffraction analysis and IR spectroscopy of a series of mono-, di-, and trinitro derivatives of phenanthrene-9,10-quinone demonstrated that the ability of carbonyl groups to participate in nucleophilic addition of water increases as the number of nitro groups in substituted phenanthrene-9,10-quinone increases. The nature of the solvent (HMPA, DMF, or DMSO) affects hydration of phenanthrenequinones primarily due to the difference in the strength of intermolecular hydrogen bonds stabilizing di- and tetrahydroxy-dihydrophenanetherenes.

Key words

10,10-dihydroxy-2,4,7-trinitro-9,10-dihydrophenanthren-9-one 10,10-dihydroxy-2,7-dinitro-9,10-dihydrophenanthren-9-one 2,5-dinitrophenanthrene-9,10-quinone hydration solvate X-ray diffraction study IR spectroscopy 

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References

  1. 1.
    G. V. Gridunova, V. E., Sliklover, Yu. T. Struchkov, R. V. Linko, A. N. Poplavskii, and A. M. Andrievskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 575 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 499 (Engl. Transl.)].Google Scholar
  2. 2.
    G. V. Gridunova, Yu. T. Struchkov, R. V. Linko, A. M. Andrievskii, and B. E. Zaitsev,Izv. Akad. Nauk, Ser. Khim., 1992, 910 [Bull. Russ. Acad. Sci., Div. Chem. Sci., 1992,41, 710 (Engl. Transl.)].Google Scholar
  3. 3.
    A. Gordon and R. Ford,The Chemist's Companion, Wiley, New York, 1972.Google Scholar
  4. 4.
    R. M. Buchanan, S. L. Kessel, H. H. Downs, C. G. Pierpont, and D. N. Hendrickson,J. Am. Chem. Soc., 1978,100, 7894.CrossRefGoogle Scholar
  5. 5.
    G. V. Gridunova, V. E. Shklover, Yu. T. Struchkov, E. N. Sidorenko, A. M. Andrievskii, Z. I. Ezhkova, and K. M. Dyumaev,Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1284 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986,35, 1163 (Engl. Transl.)].Google Scholar
  6. 6.
    F. M. Allen, O. Kennard, D. Watson, L. Brammer, G. Orpen, and R. Taylor,J. Chem. Soc., Perkin Trans. 2, 1987, S1.Google Scholar
  7. 7.
    Yu. V. Zefirov,Zh. Obshchi. Khim., 1976,46, 2636 [J. Gen. Chem. USSR, 1976,46 (Engl. Transl.)].Google Scholar
  8. 8.
    N. I. Sadova and L. V. Vilkov,Usp. Khim., 1982,51, 153 [Russ. Chem. Rev., 1982,51 (Engl. Transl.)].Google Scholar
  9. 9.
    V. A. Rabinovich and Z. Ya. Khavin,Kratkii khimicheskii spravochnik [Short Handbook of Chemistry], Khimiya Leningrad, 1977, 277 pp. (in Russian).Google Scholar
  10. 10.
    H. Becker,Einfuhrung in die Elektronentheorie Organisch-Chemisher Reaktionen, VEB Deutscher Verlag der Wissenschaften, Berlin, 1974.Google Scholar
  11. 11.
    S. Kato, M. Maezawa, S. Hirano, and T. Ishigaku,Yuki Gosei Kagaku Kyokai Shi, 1957,15, 29;Chem. Abstrs., 1958,51, 10462f,g.i.Google Scholar
  12. 12.
    T. K. Mukherjee,J. Phys. Chem., 1976,71, 2277.Google Scholar
  13. 13.
    J. Schmidt and P. Austin,Ber., 1903,36, 3734.Google Scholar
  14. 14.
    G. M. Sheldrick,SHELX-76 Program for Crystal Structure Determination, Cambridge Univ., 1976.Google Scholar
  15. 15.
    G. M. Sheldrick,Acta Crystallogr., 1990,46A, 467.Google Scholar
  16. 16.
    G. M. Sheldrick,SHELXL-93 Program for the Refinement of Crystal Structures, Univ. of Gottingen, Germany, 1994.Google Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • R. V. Linko
    • 1
  • V. A. Soldatkina
    • 1
  • B. E. Zaitsev
    • 1
  • V. I. Sokol
    • 2
  • V. V. Davydov
    • 1
  1. 1.Russian Peoples' Friendship UniversityMoscowRussian Federation
  2. 2.N. S. Kurnakov Institute of General and Inorganic ChemsitryRussian Academy of SciencesMoscowRussian Federation

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