Russian Journal of Organic Chemistry

, Volume 48, Issue 2, pp 241–248 | Cite as

Spectral and quantum-chemical investigation of ortho- and peri-hydroxy-substituted mono- and diformyl derivatives of 1,5-naphthalenediol

  • V. V. Mezheritskii
  • M. S. Korobov
  • O. M. Golyanskaya
  • N. I. Omelichkin
  • L. G. Minyaeva
  • G. S. Borodkin
  • A. A. Milov
  • A. V. Tsukanov
  • A. D. Dubonosov
Article

Abstract

Spectral and quantum-chemical investigation of ortho- and peri-hydroxy-substituted aldehydes, 1,5-naphthalenediol derivatives, was carried out. An unusual spin-spin coupling through an intramolecular hydrogen bond was discovered in the molecule of 1,5-dihydroxynaphthalene-4,8-dicarbaldehyde. It was shown that this dialdehyde is involved into the ring-chain tautomerism. The position of this equilibrium was examined depending on the temperature and the solvent polarity. The effect of the solvent polarity on the benzoid-quinoid tautomerism in the dihydroxynaphthalene-2,6-dicarbaldehyde was established. By the method of quantum-chemical calculations the relative energy stability and conformational structure of dialdehydes were revealed.

Keywords

Intramolecular Hydrogen Bond Formyl Formyl Group Separate Precipitate Covalent Contribution 

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Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • V. V. Mezheritskii
    • 1
  • M. S. Korobov
    • 1
  • O. M. Golyanskaya
    • 1
  • N. I. Omelichkin
    • 1
  • L. G. Minyaeva
    • 1
  • G. S. Borodkin
    • 1
  • A. A. Milov
    • 2
  • A. V. Tsukanov
    • 2
  • A. D. Dubonosov
    • 2
  1. 1.Institute of Physical and Organic Chemistry at the Southern Federal UniversityRostov-on-DonRussia
  2. 2.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia

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