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Using Chou’s 5-Step Rule to Evaluate the Stability of Tautomers: Susceptibility of 2-[(Phenylimino)-methyl]-cyclohexane-1,3-diones to Tautomerization Based on the Calculated Gibbs Free Energies

Author

Listed:
  • Robert Dobosz

    (Institute of Mathematics and Physics, UTP University of Science and Technology, Al. Prof. S. Kaliskiego 7, 85-796 Bydgoszcz, Poland)

  • Jan Mućko

    (Faculty of Telecommunications, Computer Science and Electrical Engineering, UTP University of Science and Technology, Al. Prof. S. Kaliskiego 7, 85-796 Bydgoszcz, Poland)

  • Ryszard Gawinecki

    (Department of Chemistry, UTP University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland)

Abstract

Gibbs free energies, based on DFT (Density Functional Theory) calculations, prove that enaminone (2-(anilinemethylidene)cyclohexane-1,3-dione) and ketamine (2-[(phenylimino)-methyl]cyclohexane-1,3-dione) are the most and least stable tautomeric forms of the studied systems, respectively. 1 H and 13 C NMR spectra prove that 2-(anilinemethylidene)cyclohexane-1,3-diones are the only tautomeric species present in dimethylsulfoxide solution (a very weak signal can be seen only for the p-methoxy derivatives). The zwitterionic character of these enaminones is strengthened by naphthoannulation and by the insertion of the electron-withdrawing substituent into the benzene ring (the latter weakens the intramolecular hydrogen bond in the compound). Substituent and naphtoannulation have no effect on the stability of the studied tautomers. Slight twisting of the benzene ring, with respect to the C Ar NC plane (seen in the crystalline state), was proven to also take place in vacuum and in solution.

Suggested Citation

  • Robert Dobosz & Jan Mućko & Ryszard Gawinecki, 2020. "Using Chou’s 5-Step Rule to Evaluate the Stability of Tautomers: Susceptibility of 2-[(Phenylimino)-methyl]-cyclohexane-1,3-diones to Tautomerization Based on the Calculated Gibbs Free Energies," Energies, MDPI, vol. 13(1), pages 1-14, January.
    • Handle: RePEc:gam:jeners:v:13:y:2020:i:1:p:183-:d:304097
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    References listed on IDEAS

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    1. Bo OuYang & Shiqi Xie & Marcelo J. Berardi & Xinhao Zhao & Jyoti Dev & Wenjing Yu & Bing Sun & James J. Chou, 2013. "Unusual architecture of the p7 channel from hepatitis C virus," Nature, Nature, vol. 498(7455), pages 521-525, June.
    2. Marcelo J. Berardi & William M. Shih & Stephen C. Harrison & James J. Chou, 2011. "Mitochondrial uncoupling protein 2 structure determined by NMR molecular fragment searching," Nature, Nature, vol. 476(7358), pages 109-113, August.
    3. Jason R. Schnell & James J. Chou, 2008. "Structure and mechanism of the M2 proton channel of influenza A virus," Nature, Nature, vol. 451(7178), pages 591-595, January.
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