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Benzenoid-quinoid tautomerism of azomethines and their structural analogs 56. Azomethine imines, derivatives of salicylic and 2-hydroxynaphthoic aldehydes

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Abstract

A study by IR, electronic and NMR (1Н and 13С) spectroscopy together with X-ray structure analysis and quantum chemical calculations using DFT B3LYP/6-31G(d,p) determined N,N´-cyclic azomethine imines — 1-(2-hydroxyphenylmethylidene)-3-oxo-5-phenylpyrazolydin-1-ium-2-yde (1) и 1-[(2-hydroxynaphthalene-1-yl)methylidene]-3-oxo-5-phenylpyrazolydin-1-ium-2-yde (2) — to exist in solutions as isomers with an intramolecular hydrogen bond between the hydroxyl group and the nitrogen of the pyrazolidone ring. Compound 1 undergoes photoexcitation in the wavelength range 363—320 nm followed by luminescence with an anomalous Stokes shift that is caused by the intramolecular excited state proton transfer mechanism (ESIPT effect).

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    O. S. Popova, V. A. Bren’, K. S. Tikhomirova, G. S. Borodkin & V. I. Minkin

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Sakharova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. V. Tkachev, A. N. Utenyshev, G. V. Shilov & S. M. Aldoshin

  3. Southern Scientific Center, Russian Academy of Sciences, 41 prosp. Chekhova, 344006, Rostov-on-Don, Russian Federation

    Yu. V. Revinskii, A. G. Starikov & A. D. Dubonosov

Authors
  1. O. S. Popova
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  2. V. A. Bren’
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  3. V. V. Tkachev
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  4. A. N. Utenyshev
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  5. Yu. V. Revinskii
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  6. K. S. Tikhomirova
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  7. A. G. Starikov
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  8. G. S. Borodkin
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  9. A. D. Dubonosov
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  10. G. V. Shilov
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  11. S. M. Aldoshin
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  12. V. I. Minkin
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Corresponding author

Correspondence to V. A. Bren’.

Additional information

For Part 55 see Ref. 1.

Dedicated to Academician of the Russian Academy of Sciences V. M. Novotortsev on the occasion of his 70-th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0648—0653, March, 2016.

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Popova, O.S., Bren’, V.A., Tkachev, V.V. et al. Benzenoid-quinoid tautomerism of azomethines and their structural analogs 56. Azomethine imines, derivatives of salicylic and 2-hydroxynaphthoic aldehydes. Russ Chem Bull 65, 648–653 (2016). https://doi.org/10.1007/s11172-016-1350-y

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  • DOI: https://doi.org/10.1007/s11172-016-1350-y

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