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Tautomerism of nitro compounds

Communication 4: Mechanism of tautomeric transformations of nitro compounds

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    All the data on the dissociation and isomerization kinetics of phenylnitromethane and nitropropane in aqueous solutions corresponds with a tautomerization mechanism of the nitro compounds in which: a) mutual transformation of the nitro- and aci-forms goes through a stage where they are dissociated. Dissociation of the nitro-form and the aci-form produces the same ion. A second form of the anion is not found to exist kinetically; b) dissociation and recombination of the nitro-forms goes comparatively slowly; c) the dissociation and recombination rate of the aci-form is several orders of magnitude higher in the corresponding rates for the nitro-form.

  2. 2.

    The reactions studied completely obey the laws governing acid-base protolytic reactions.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, USSR

    V. M. Belikov, S. G. Mairanovskii, Ts. B. Korchemnaya & S. S. Novikov

Authors
  1. V. M. Belikov
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  2. S. G. Mairanovskii
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  3. Ts. B. Korchemnaya
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  4. S. S. Novikov
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Belikov, V.M., Mairanovskii, S.G., Korchemnaya, T.B. et al. Tautomerism of nitro compounds. Russ Chem Bull 11, 560–567 (1962). https://doi.org/10.1007/BF00904752

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  • DOI: https://doi.org/10.1007/BF00904752

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