IDEAS home Printed from https://ideas.repec.org/a/gam/jeners/v13y2020i1p183-d304097.html
   My bibliography  Save this article

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
    as

    Download full text from publisher

    File URL: https://www.mdpi.com/1996-1073/13/1/183/pdf
    Download Restriction: no

    File URL: https://www.mdpi.com/1996-1073/13/1/183/
    Download Restriction: no
    ---><---

    References listed on IDEAS

    as
    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. 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.
    3. 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.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Bi-Qing Li & Le-Le Hu & Lei Chen & Kai-Yan Feng & Yu-Dong Cai & Kuo-Chen Chou, 2012. "Prediction of Protein Domain with mRMR Feature Selection and Analysis," PLOS ONE, Public Library of Science, vol. 7(6), pages 1-14, June.
    2. Antoine Gagelin & Corentin Largeau & Sandrine Masscheleyn & Mathilde S. Piel & Daniel Calderón-Mora & Frédéric Bouillaud & Jérôme Hénin & Bruno Miroux, 2023. "Molecular determinants of inhibition of UCP1-mediated respiratory uncoupling," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    3. Kuo-Chen Chou & Hong-Bin Shen, 2010. "A New Method for Predicting the Subcellular Localization of Eukaryotic Proteins with Both Single and Multiple Sites: Euk-mPLoc 2.0," PLOS ONE, Public Library of Science, vol. 5(4), pages 1-9, April.
    4. Kuo-Chen Chou & Hong-Bin Shen, 2010. "Plant-mPLoc: A Top-Down Strategy to Augment the Power for Predicting Plant Protein Subcellular Localization," PLOS ONE, Public Library of Science, vol. 5(6), pages 1-11, June.
    5. L. Eyer & K. Hruska, 2013. "Antiviral agents targeting the influenza virus: a review and publication analysis," Veterinární medicína, Czech Academy of Agricultural Sciences, vol. 58(3), pages 113-185.
    6. Mattia L DiFrancesco & Ulf-Peter Hansen & Gerhard Thiel & Anna Moroni & Indra Schroeder, 2014. "Effect of Cytosolic pH on Inward Currents Reveals Structural Characteristics of the Proton Transport Cycle in the Influenza A Protein M2 in Cell-Free Membrane Patches of Xenopus oocytes," PLOS ONE, Public Library of Science, vol. 9(9), pages 1-12, September.
    7. Jianzhao Gao & Wei Cui & Yajun Sheng & Jishou Ruan & Lukasz Kurgan, 2016. "PSIONplus: Accurate Sequence-Based Predictor of Ion Channels and Their Types," PLOS ONE, Public Library of Science, vol. 11(4), pages 1-18, April.
    8. Zhisong He & Jian Zhang & Xiao-He Shi & Le-Le Hu & Xiangyin Kong & Yu-Dong Cai & Kuo-Chen Chou, 2010. "Predicting Drug-Target Interaction Networks Based on Functional Groups and Biological Features," PLOS ONE, Public Library of Science, vol. 5(3), pages 1-8, March.
    9. Xingya Li & Gengping Jiang & Meipeng Jian & Chen Zhao & Jue Hou & Aaron W. Thornton & Xinyi Zhang & Jefferson Zhe Liu & Benny D. Freeman & Huanting Wang & Lei Jiang & Huacheng Zhang, 2023. "Construction of angstrom-scale ion channels with versatile pore configurations and sizes by metal-organic frameworks," Nature Communications, Nature, vol. 14(1), pages 1-12, December.

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:gam:jeners:v:13:y:2020:i:1:p:183-:d:304097. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: MDPI Indexing Manager (email available below). General contact details of provider: https://www.mdpi.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.