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The equilibrium between the iso and the normal forms of 9-nitrofluorene

  • K. D. Nenitzescu
  • I. G. Dinulescu
Organic and Biological Chemistry

Summary

  1. 1.

    A series of bromometric titrations of solution of iso-9-nitrofluorene in ethanol, dioxane and benzene was run.

     
  2. 2.

    The iso-form is thermodynamically more stable in the crystalline form than is the normal form; equilibria are established in solution in which the content of the normal form is greater with lower polarity of the solvent. The normal form of 9-nitrofluorene cannot be isolated since it disproportionates forming 1,2-dinitro1,2-dibiphenylene-ethane and fluorenone oxime. This reaction occurs at a lower rate than the reaction of formation of the normal form from the iso-form. Consequently, temporarily large concentrations of the normal form exist in solution and these were established by a chemical route.

     
  3. 3.

    The greater stability of the iso-form of 9-nitrofluorene is determined by the tendency of the cyclopentadiene ring to form an aromatic sextet by attracting electron pairs from the nitro group.

     

Keywords

Benzene Titration Normal Form Dioxane Oxime 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Consultants Bureau Inc. 1959

Authors and Affiliations

  • K. D. Nenitzescu
    • 1
  • I. G. Dinulescu
    • 1
  1. 1.Division of Chemical Research of the Academy of Rumanian Peoples RepublicRumania

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