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Russian Journal of Organic Chemistry

, Volume 52, Issue 4, pp 541–545 | Cite as

Benzoid–Quinoid tautomerism of schiff bases and their structural analogs: LVII. 2-[(3-oxo-5-phenylpyrazolidin-1-yl)methylidene]-1H-indene-1,3(2H)-dione

  • O. S. Popova
  • V. A. Bren’
  • V. V. Tkachev
  • A. N. Utenyshev
  • Yu. V. Revinskii
  • K. S. Tikhomirova
  • A. G. Starikov
  • G. S. Borodkin
  • A. D. Dubonosov
  • I. E. Tolpygin
  • G. V. Shilov
  • S. M. Aldoshin
  • V. I. Minkin
Review
  • 47 Downloads

Abstract

Potentially tautomeric azomethine imide, 2-[(3-oxo-5-phenylpyrazolidin-1-yl)methylidene]-1H-indene- 1,3(2H)-dione, has been synthesized by condensation of 5-phenylpyrazolidin-3-one with 2-(hydroxymethylidene)-1H-indene-1,3(2H)-dione. According to the IR, 1H and 13C NMR, and electronic absorption spectroscopy data and DFT B3LYP/6-311++G(d,p) quantum chemical calculations, the title compound in solution exists as planar tricarbonyl tautomer stabilized by intramolecular hydrogen bond between the NH proton of the pyrazolidine fragment and carbonyl oxygen atom of the indene fragment. Its crystal structure was determined by X-ray analysis.

Keywords

Methylidene Indandione Pyrazolidine COSMO Model Indene Fragment 
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

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • O. S. Popova
    • 1
  • V. A. Bren’
    • 1
  • V. V. Tkachev
    • 2
  • A. N. Utenyshev
    • 2
  • Yu. V. Revinskii
    • 3
  • K. S. Tikhomirova
    • 1
  • A. G. Starikov
    • 3
  • G. S. Borodkin
    • 1
  • A. D. Dubonosov
    • 3
  • I. E. Tolpygin
    • 1
  • G. V. Shilov
    • 2
  • S. M. Aldoshin
    • 2
  • V. I. Minkin
    • 1
    • 3
  1. 1.Research Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussia
  2. 2.Institute of Chemical Physics ProblemsRussian Academy of SciencesChernogolovka, Moscow oblastRussia
  3. 3.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia

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