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Investigations on nitropyrroles

Communication 3. Ultraviolet absorption spectra and tautomeric transformations of some nitropyrroles

Summary

  1. 1.

    The ultraviolet spectra of eight nitropyrroles were studied.

  2. 2.

    It was shown that ultraviolet spectroscopy may be used to determine the position of an NO2 group in a pyrrole nucleus and the structure proposed previously for 1-methyl-3,4-dinitropyrrole was confirmed.

  3. 3.

    Tautomerism in nitropyrroles unsubstituted at the nitrogen was investigated and it was shown that the acidity of these compounds increases with an increase in the number of nitro groups and with transfer of nitro groups from the β to α positions. This phenomenon is apparently connected with the Inductive effect of a nitro group on the polarization of the N−H bond.

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Literature cited

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Novikov, S.S., Belikov, V.M., Egorov, Y.P. et al. Investigations on nitropyrroles. Russ Chem Bull 8, 1386–1392 (1959). https://doi.org/10.1007/BF00918580

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Keywords

  • Nitrogen
  • Spectroscopy
  • Acidity
  • Pyrrole
  • Nitro Group