Skip to main content
SpringerLink
Log in

The ionization potentials of alkoxymethyldialkylamines and the anomeric effect

  • Physical Chemistry
  • Structure And Physicochemical Characteristics Of Molecules
  • Published:
Bulletin of the Russian Academy of Sciences, Division of chemical science Aims and scope

Abstract

The ionization potentials IP1(nN) and IP2(nO) of alkoxymethyldialkylamines ROCH2NEt2 and MeOCH2NR2 were determined by photoelectron (PE) spectroscopy, and the conduction of the electronic effects of the substituents was studied. The anomeric nN-σ*(C-O) interaction was appraised by comparison of the ionization potentials. Interaction between the nO and σ*(C-N) orbitals was not detected. The energies of charge transfer, strengthening of the N-C bond, and weakening of the C-O bond, due to the nN-σ*(C-O) interaction, were determined.

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. V. Zverev, A. A. Bredikhin, V. M. Vakar', and A. N. Vereshchagin,Zh. Strukt. Khim. 27, 64 (1986).

    Google Scholar 

  2. V. V. Zverev,Zh. Obshch. Khim. 60, No. 12, 2524 (1990).

    Google Scholar 

  3. V. V. Zverev,Zh. Org. Khim. 22, No. 2, 465 (1986).

    Google Scholar 

  4. M. Krol, C. Huige, and C. Altona,J. Computational Chem. 11, 765 (1990).

    Google Scholar 

  5. H. Hellmann and G. Opitz,α-Aminoalkylierung Verlag Chemie, Weinheim (1960).

    Google Scholar 

  6. R. Benno,Die Mannich-Reaction, Berlin (1959).

  7. H. T. Stewart and C. R. Hauser,J. Am. Chem. Soc. 77, 1098 (1955).

    Google Scholar 

  8. H. B'hme and H. G. Viehe,Iminium Salts in Organic Chemistry. Part 1. Advances in Organic Chemistry: Methods and Results (Editor E. C. Taylor), Wiley, New York, London, Toronto (1960).

    Google Scholar 

  9. B. E. Fields,J. Am. Chem. Soc. 74, 1528 (1952).

    Google Scholar 

  10. Dietsche,Ann. Chem. 12, 712 (1968).

    Google Scholar 

  11. B. E. Ivanov and S. S. Krokhina,Izv. Akad. Nauk, Ser. Khim., No. 12, 2782 (1967); No. 2, 424 (1967).

  12. R. G. Kostyanovskii, Yu. I. Él'natanov, and Sh. M. Shikhaliev,Izv. Akad. Nauk, Ser. Khim., No. 1, 249 (1977).

Download references

Authors
  1. V. V. Zverev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. K. Badeeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. S. Krokhina
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan' Scientific Center, Russian Academy of Sciences, 420083 Kazan'. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 6, pp. 1356–1358, June, 1992.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zverev, V.V., Badeeva, E.K. & Krokhina, S.S. The ionization potentials of alkoxymethyldialkylamines and the anomeric effect. Russ Chem Bull 41, 1058–1059 (1992). https://doi.org/10.1007/BF00866585

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00866585

Key words

Search

Navigation