International Journal of Computational and Theoretical Chemistry

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Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases

Received: 31 January 2019    Accepted: 15 March 2019    Published: 03 April 2019
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Abstract

This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.

DOI 10.11648/j.ijctc.20190701.17
Published in International Journal of Computational and Theoretical Chemistry (Volume 7, Issue 1, June 2019)
Page(s) 49-55
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

2-Thioxanthine, Stability, Tautomerism, Acidity, B3LYP

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Author Information
  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

  • Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

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  • APA Style

    Assoma Amon Benjamine, Koné Mawa, Alao Latifatou Laye, Bede Affoué Lucie, Koné Soleymane, et al. (2019). Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. International Journal of Computational and Theoretical Chemistry, 7(1), 49-55. https://doi.org/10.11648/j.ijctc.20190701.17

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    ACS Style

    Assoma Amon Benjamine; Koné Mawa; Alao Latifatou Laye; Bede Affoué Lucie; Koné Soleymane, et al. Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. Int. J. Comput. Theor. Chem. 2019, 7(1), 49-55. doi: 10.11648/j.ijctc.20190701.17

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    AMA Style

    Assoma Amon Benjamine, Koné Mawa, Alao Latifatou Laye, Bede Affoué Lucie, Koné Soleymane, et al. Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. Int J Comput Theor Chem. 2019;7(1):49-55. doi: 10.11648/j.ijctc.20190701.17

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  • @article{10.11648/j.ijctc.20190701.17,
      author = {Assoma Amon Benjamine and Koné Mawa and Alao Latifatou Laye and Bede Affoué Lucie and Koné Soleymane and N’Guessan Boka Robert and Bamba El Hadji Sawaliho and N’guessan Yao Thomas},
      title = {Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases},
      journal = {International Journal of Computational and Theoretical Chemistry},
      volume = {7},
      number = {1},
      pages = {49-55},
      doi = {10.11648/j.ijctc.20190701.17},
      url = {https://doi.org/10.11648/j.ijctc.20190701.17},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.ijctc.20190701.17},
      abstract = {This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.},
     year = {2019}
    }
    

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  • TY  - JOUR
    T1  - Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases
    AU  - Assoma Amon Benjamine
    AU  - Koné Mawa
    AU  - Alao Latifatou Laye
    AU  - Bede Affoué Lucie
    AU  - Koné Soleymane
    AU  - N’Guessan Boka Robert
    AU  - Bamba El Hadji Sawaliho
    AU  - N’guessan Yao Thomas
    Y1  - 2019/04/03
    PY  - 2019
    N1  - https://doi.org/10.11648/j.ijctc.20190701.17
    DO  - 10.11648/j.ijctc.20190701.17
    T2  - International Journal of Computational and Theoretical Chemistry
    JF  - International Journal of Computational and Theoretical Chemistry
    JO  - International Journal of Computational and Theoretical Chemistry
    SP  - 49
    EP  - 55
    PB  - Science Publishing Group
    SN  - 2376-7308
    UR  - https://doi.org/10.11648/j.ijctc.20190701.17
    AB  - This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.
    VL  - 7
    IS  - 1
    ER  - 

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