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


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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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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