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Chemistry of Heterocyclic Compounds

, Volume 8, Issue 10, pp 1249–1252 | Cite as

Electronic absorption spectra and protolysis of 4- and 5-azaindan-1,3-diones

  • I. V. Turovskii
  • O. Ya. Neiland
  • L. É. Neiland
  • Ya. P. Stradyn'
Article
  • 26 Downloads

Abstract

The protolytic equilibria in a series of 2-aryl-substituted 4- and 5-azaindan-1,3-diones and the corresponding N-methylbetaines and 5,6-benzo analogs were studied by spectrophotometry. The substantial difference between the 4- and 5-aza derivatives is explained by the different effect of the anionic system on the Tr-electron density and the reactivities of the nitrogen atoms in the 4 and 5 positions. The protonation and deprotonation constants of the dipolar ions correlate linearly with the σ constants of the substituents in the 2-phenyl ring. In the case of 5,6-benzo-4-azaindan-1,3-diones, the keto group of the azaphthaloyl ring is protonated along with the dipolar ion in strongly acidic media.

Keywords

Nitrogen Organic Chemistry Absorption Spectrum Nitrogen Atom Diones 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • I. V. Turovskii
    • 1
  • O. Ya. Neiland
    • 1
  • L. É. Neiland
    • 1
  • Ya. P. Stradyn'
    • 1
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga

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