Skip to main content
SpringerLink
Log in

Dependence of the reactivity of five-membered aromatic heterocycles on their structure. 5. Protonation of furazane, furoxane, and their aminoderivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Proton affinity of furazane, furoxane, and their aminoderivatives for protonation at various centers was calculated by ab initio methods using the STO-3G basis set. Basicity was found to decrease in the following order: N-oxide oxygen atom, endocyclic nitrogen atom, amino group. The presence in the ring of aminogroups or N-oxide functions leads to elevated proton affinity of the basic centers which are located in the active positions of the ring.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  1. V. G. Andrianov, M. A. Shokhen, and A. V. Eremeev, Khim. Geterotsikl. Soedin., No. 9, 1221 (1989).

    Google Scholar 

  2. J. Elguero, C. Marzin, A. R. Katritzky, and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York, San Francisco, and London (1976), p. 413.

    Google Scholar 

  3. V. G. Andrianov, M. A. Shokhen, A. V. Eremeev, and S. V. Barmina, Khim. Geterotsikl. Soedin., No. 1, 54 (1987).

    Google Scholar 

  4. D. Viterbo and A. Serafino, Acta Cryst. Sect. B, Struct. Crystallogr. Cryst. Chem., 34, 3444 (1978).

    Google Scholar 

  5. B. T. Storey, W. W. Sullivan, and C. L. Moyer, J. Org. Chem., 29, 3118 (1964).

    Google Scholar 

  6. J. Elguero, E. Gonzalez, and R. Jacquier, Bull. Soc. Chim. Fr., No. 10, 5009 (1968).

    Google Scholar 

  7. I. I. Grandberg, S. V. Tabak, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 1, 85 (1966).

    Google Scholar 

  8. G. Dedichen, Berichte, 39, 1831 (1906).

    Google Scholar 

  9. M. G. Voronkov, T. V. Kamik, V. V. Makarskii, V. A. Lopyrev, S. M. Ponomareva, and E. F. Shibanova, Dokl. Akad. Nauk, 227, 1116 (1976).

    Google Scholar 

  10. I. V. Tselinskii, S. F. Mel'nikova, and S. N. Vergizov, Khim. Geterotsikl, Soedin., No. 3, 321 (1981).

    Google Scholar 

  11. A. F. Pozharskii, Theoretical Principles of Heterocyclic Chemistry [in Russian], Khimiya, Moscow (1985), p. 119.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006, Riga

    V. G. Andrianov, M. A. Shokhen & A. V. Eremeev

Authors
  1. V. G. Andrianov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. Shokhen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Eremeev
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 4, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1261–1264, September, 1989.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Andrianov, V.G., Shokhen, M.A. & Eremeev, A.V. Dependence of the reactivity of five-membered aromatic heterocycles on their structure. 5. Protonation of furazane, furoxane, and their aminoderivatives. Chem Heterocycl Compd 25, 1056–1059 (1989). https://doi.org/10.1007/BF00487310

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00487310

Keywords

Search

Navigation