Skip to main content
Log in

Acidic properties and structure of pyrrolanthrones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The NH acidity of pyrrolanthrone in dimethyl sulfoxide and the COOH acidity of pyrrolanthrone-1-carboxylic acid exceed the acidities of indole and indole-2-carboxylic acid by 6 and 2.5 orders of magnitude, respectively; this is due to the electron-acceptor effect of the condensed anthrone ring. A quantitative estimate of the effect of substituents in the 1 position on the NH acidity indicates that the bonds in the pyrrole fragment are localized to a significant degree; the C1-N bond approaches a single bond, and the C1-C10b bond consequently approaches a double bond. The effect on the NH acidity of NO2 and NH2 groups located in the anthrone fragment (in the 5 position) is examined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. M. V. Kazankov, N. P. Makshanova, and E. G. Kuznetsova, Khim. Geterotsikl. Soedin., No. 8, 1103 (1977).

    Google Scholar 

  2. M. V. Kazankov and E. G. Sadovykh, Khim. Geterotsikl. Soedin., No. 6, 785 (1978).

    Google Scholar 

  3. M. V. Kazankov and E. G. Sadovykh, Khim. Geterotsikl. Soedin., No. 10, 1356 (1978).

    Google Scholar 

  4. M. K. A. Khan and K. J. Morgan, Tetrahedron, 21, 2197 (1965).

    Google Scholar 

  5. M. Lautie, M. H. Limage, and A. Novak, Spectrochim. Acta, 33A, 121 (1977).

    Google Scholar 

  6. W. J. Houlihan (ed.), The Chemistry of Heterocyclic Compounds. Indoles. Part 1, Vol. 25, Wiley, New York (1972), pp. 208, 411.

    Google Scholar 

  7. M. Charton, J. Am. Chem. Soc., 86, 2033 (1964).

    Google Scholar 

  8. F. G. Bordwell, D. Algrim, and N. R. Vanier, J. Org. Chem., 42, 1817 (1977).

    Google Scholar 

  9. K. Kalfus, J. Slosar, V. Sterba, and M. Vecera, Coll. Czech. Chem. Commun., 34, 2083 (1969).

    Google Scholar 

  10. B. A. Korolev, T. V. Levandovskaya, and M. V. Gorelik, Zh. Obshch. Khim., 48, 157 (1978).

    Google Scholar 

  11. Dictionary of Organic Compounds, Vol. 3, London (1965), pp. 1846, 1847.

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1659–1661, December, 1979.

Original article submitted April 5, 1979.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kazankov, M.V., Sadovykh, E.G. & Korolev, B.A. Acidic properties and structure of pyrrolanthrones. Chem Heterocycl Compd 15, 1334–1337 (1979). https://doi.org/10.1007/BF00514738

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00514738

Keywords

Navigation