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A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives

Received: 28 May 2019    Accepted: 20 September 2019    Published: 29 September 2019
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Abstract

The 2-phenylbenzothiazole derivatives have antitumor activities. Work has shown that these derivatives have mesomeric forms. The electrophilic centers of these mesomers form adducts with the nucleophilic centers of deoxyribonucleic acid (DNA). These adducts destroy the tumor cells and prevent the proliferation of these. In this sense, the knowledge of electrophilic sites, nucleophiles and the capacity to protonate these derivatives is therefore useful if we want to know their future in the biological environment. Using DFT/B3LYP method associated with the bases 6-31G (d, p) and 6-31+G (d, p), this work aims at determining the preferential protonation site, the electrophilic and nucleophilic centers of six 2-phenylbenzothiazole. This study also analyzes the stability of these derivatives. Calculations are carried out in gas and aqueous phases. Results show that fluorinated derivatives are the most stable. 2-(4-aminophenyl) benzothiazoles are the most reactive. The atoms carbon C4, C5 and C6 of benzothiazole ring are the most electrophilic. Interactions of these derivatives with nucleophilic centers of deoxyribonucleic acid (DNA) will probably be at these atoms. Nitrogen sp2 (N1) of benzothiazole ring remains the most nucleophilic center and the preferential site of protonation in all the molecules studied. These results highlight the influence of the substituents on the basicity of the nitrogen sp2 (N1) and reactivity of the 2-phenylbenzothiazole derivatives studied.

DOI 10.11648/j.mc.20190703.14
Published in Modern Chemistry (Volume 7, Issue 3, September 2019)

This article belongs to the Special Issue Advanced Journal of Chemistry

Page(s) 65-72
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-Phenylbenzothiazole, Energetic Gaps, Fukui Indices, Protonic Affinity, DFT/B3LYP

References
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Author Information
  • Unit Formation and Research of Sciences of Structures of Matter and Technology (UFR SSMT), University Felix Houphou?t-Boigny, Abidjan, Ivory Coast

  • Unit Formation and Research of Sciences of Structures of Matter and Technology (UFR SSMT), University Felix Houphou?t-Boigny, Abidjan, Ivory Coast

  • Unit Formation and Research of Sciences of Structures of Matter and Technology (UFR SSMT), University Felix Houphou?t-Boigny, Abidjan, Ivory Coast

  • Unit Formation and Research of Sciences of Structures of Matter and Technology (UFR SSMT), University Felix Houphou?t-Boigny, Abidjan, Ivory Coast

  • it Formation and Research of Sciences Fondamental and Applied (UFR SFA), University Nangui Abrogoua, Abidjan, Ivory Coast

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    Bede Affoue Lucie, Kone Soleymane, N’Guessan Boka Robert, Yapo Kicho Denis, Ziao Nahosse. (2019). A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives. Modern Chemistry, 7(3), 65-72. https://doi.org/10.11648/j.mc.20190703.14

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    ACS Style

    Bede Affoue Lucie; Kone Soleymane; N’Guessan Boka Robert; Yapo Kicho Denis; Ziao Nahosse. A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives. Mod. Chem. 2019, 7(3), 65-72. doi: 10.11648/j.mc.20190703.14

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    AMA Style

    Bede Affoue Lucie, Kone Soleymane, N’Guessan Boka Robert, Yapo Kicho Denis, Ziao Nahosse. A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives. Mod Chem. 2019;7(3):65-72. doi: 10.11648/j.mc.20190703.14

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  • @article{10.11648/j.mc.20190703.14,
      author = {Bede Affoue Lucie and Kone Soleymane and N’Guessan Boka Robert and Yapo Kicho Denis and Ziao Nahosse},
      title = {A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives},
      journal = {Modern Chemistry},
      volume = {7},
      number = {3},
      pages = {65-72},
      doi = {10.11648/j.mc.20190703.14},
      url = {https://doi.org/10.11648/j.mc.20190703.14},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.mc.20190703.14},
      abstract = {The 2-phenylbenzothiazole derivatives have antitumor activities. Work has shown that these derivatives have mesomeric forms. The electrophilic centers of these mesomers form adducts with the nucleophilic centers of deoxyribonucleic acid (DNA). These adducts destroy the tumor cells and prevent the proliferation of these. In this sense, the knowledge of electrophilic sites, nucleophiles and the capacity to protonate these derivatives is therefore useful if we want to know their future in the biological environment. Using DFT/B3LYP method associated with the bases 6-31G (d, p) and 6-31+G (d, p), this work aims at determining the preferential protonation site, the electrophilic and nucleophilic centers of six 2-phenylbenzothiazole. This study also analyzes the stability of these derivatives. Calculations are carried out in gas and aqueous phases. Results show that fluorinated derivatives are the most stable. 2-(4-aminophenyl) benzothiazoles are the most reactive. The atoms carbon C4, C5 and C6 of benzothiazole ring are the most electrophilic. Interactions of these derivatives with nucleophilic centers of deoxyribonucleic acid (DNA) will probably be at these atoms. Nitrogen sp2 (N1) of benzothiazole ring remains the most nucleophilic center and the preferential site of protonation in all the molecules studied. These results highlight the influence of the substituents on the basicity of the nitrogen sp2 (N1) and reactivity of the 2-phenylbenzothiazole derivatives studied.},
     year = {2019}
    }
    

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  • TY  - JOUR
    T1  - A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives
    AU  - Bede Affoue Lucie
    AU  - Kone Soleymane
    AU  - N’Guessan Boka Robert
    AU  - Yapo Kicho Denis
    AU  - Ziao Nahosse
    Y1  - 2019/09/29
    PY  - 2019
    N1  - https://doi.org/10.11648/j.mc.20190703.14
    DO  - 10.11648/j.mc.20190703.14
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
    SP  - 65
    EP  - 72
    PB  - Science Publishing Group
    SN  - 2329-180X
    UR  - https://doi.org/10.11648/j.mc.20190703.14
    AB  - The 2-phenylbenzothiazole derivatives have antitumor activities. Work has shown that these derivatives have mesomeric forms. The electrophilic centers of these mesomers form adducts with the nucleophilic centers of deoxyribonucleic acid (DNA). These adducts destroy the tumor cells and prevent the proliferation of these. In this sense, the knowledge of electrophilic sites, nucleophiles and the capacity to protonate these derivatives is therefore useful if we want to know their future in the biological environment. Using DFT/B3LYP method associated with the bases 6-31G (d, p) and 6-31+G (d, p), this work aims at determining the preferential protonation site, the electrophilic and nucleophilic centers of six 2-phenylbenzothiazole. This study also analyzes the stability of these derivatives. Calculations are carried out in gas and aqueous phases. Results show that fluorinated derivatives are the most stable. 2-(4-aminophenyl) benzothiazoles are the most reactive. The atoms carbon C4, C5 and C6 of benzothiazole ring are the most electrophilic. Interactions of these derivatives with nucleophilic centers of deoxyribonucleic acid (DNA) will probably be at these atoms. Nitrogen sp2 (N1) of benzothiazole ring remains the most nucleophilic center and the preferential site of protonation in all the molecules studied. These results highlight the influence of the substituents on the basicity of the nitrogen sp2 (N1) and reactivity of the 2-phenylbenzothiazole derivatives studied.
    VL  - 7
    IS  - 3
    ER  - 

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