International Journal of Computational and Theoretical Chemistry

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Theoretical Study of Tautomeric Equilibrium, the Stability, Polarizability, HOMO-LUMO Analysis and Acidity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one Derivatives

Received: Aug. 13, 2019    Accepted: Aug. 28, 2019    Published: Sep. 11, 2019
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Abstract

Quinoline derivatives have several reactionnels sites conferring them a hight reactivity. This makes them excellent precursors in the synthesis of new bioactive compounds. Considering the interest of quinoline chemistry and diversity of their applications, a study based on a theoretical approach of reactivity of 4,4-dimethyl-3,4-dihydro-quinolin-2(1H)-one and derivatives is carried. This study determines interaction sites of these derivatives in order to understand the mechanisms involved. Calculations are carried in gaseous phase and solution in N, N-dimethylformamide (DMF). Density Functional Theory (DFT/B3LYP) method associated with 6-311G(d) and 6-311+G (d) bases is used to perform these calculations. Results of the thermodynamic parameters showed that there is a tautomeric equilibrium relationship between the different derivatives Reactivity analysis based on Frontier Molecular Orbitals theory revealed that tautomers ketone are less reactive than tautomers enol. Calculation of Fukui indices indicates that the carbon atoms C2, C3, C5, C 7 and C8 of quinoline-2-one ring are sites favorable to nucleophilic attack. Atoms N1, C4, C6 and O11 are nucleophilic sites therefore favorable to an electrophilic attack. Methoxyl substituent (CH3O) decreases the acidity of nitrogen and oxygen atoms of quinolin-2-one while bromine atom increases acidity of these same sites. These results predict a deprotonation of the nitrogen (N1) of the brominated quinoline-2-ones less energetic than that of the methoxylated derivatives. Conclusively, this work provides data to elucidate the mechanisms to understand the reactivity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one derivatives.

DOI 10.11648/j.ijctc.20190702.11
Published in International Journal of Computational and Theoretical Chemistry ( Volume 7, Issue 2, December 2019 )
Page(s) 107-114
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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.

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

Keywords

Theoretical Study of Tautomeric Equilibrium, the Stability, Polarizability, HOMO-LUMO Analysis and Acidity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one Derivatives

References
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    Lucie Affoue Bede, Benjamine Amon Assoma, Latyfatou Laye Alao, Denis Kicho Yapo, Soleymane Kone. (2019). Theoretical Study of Tautomeric Equilibrium, the Stability, Polarizability, HOMO-LUMO Analysis and Acidity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one Derivatives. International Journal of Computational and Theoretical Chemistry, 7(2), 107-114. https://doi.org/10.11648/j.ijctc.20190702.11

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    ACS Style

    Lucie Affoue Bede; Benjamine Amon Assoma; Latyfatou Laye Alao; Denis Kicho Yapo; Soleymane Kone. Theoretical Study of Tautomeric Equilibrium, the Stability, Polarizability, HOMO-LUMO Analysis and Acidity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one Derivatives. Int. J. Comput. Theor. Chem. 2019, 7(2), 107-114. doi: 10.11648/j.ijctc.20190702.11

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    AMA Style

    Lucie Affoue Bede, Benjamine Amon Assoma, Latyfatou Laye Alao, Denis Kicho Yapo, Soleymane Kone. Theoretical Study of Tautomeric Equilibrium, the Stability, Polarizability, HOMO-LUMO Analysis and Acidity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one Derivatives. Int J Comput Theor Chem. 2019;7(2):107-114. doi: 10.11648/j.ijctc.20190702.11

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  • @article{10.11648/j.ijctc.20190702.11,
      author = {Lucie Affoue Bede and Benjamine Amon Assoma and Latyfatou Laye Alao and Denis Kicho Yapo and Soleymane Kone},
      title = {Theoretical Study of Tautomeric Equilibrium, the Stability, Polarizability, HOMO-LUMO Analysis and Acidity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one Derivatives},
      journal = {International Journal of Computational and Theoretical Chemistry},
      volume = {7},
      number = {2},
      pages = {107-114},
      doi = {10.11648/j.ijctc.20190702.11},
      url = {https://doi.org/10.11648/j.ijctc.20190702.11},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.ijctc.20190702.11},
      abstract = {Quinoline derivatives have several reactionnels sites conferring them a hight reactivity. This makes them excellent precursors in the synthesis of new bioactive compounds. Considering the interest of quinoline chemistry and diversity of their applications, a study based on a theoretical approach of reactivity of 4,4-dimethyl-3,4-dihydro-quinolin-2(1H)-one and derivatives is carried. This study determines interaction sites of these derivatives in order to understand the mechanisms involved. Calculations are carried in gaseous phase and solution in N, N-dimethylformamide (DMF). Density Functional Theory (DFT/B3LYP) method associated with 6-311G(d) and 6-311+G (d) bases is used to perform these calculations. Results of the thermodynamic parameters showed that there is a tautomeric equilibrium relationship between the different derivatives Reactivity analysis based on Frontier Molecular Orbitals theory revealed that tautomers ketone are less reactive than tautomers enol. Calculation of Fukui indices indicates that the carbon atoms C2, C3, C5, C 7 and C8 of quinoline-2-one ring are sites favorable to nucleophilic attack. Atoms N1, C4, C6 and O11 are nucleophilic sites therefore favorable to an electrophilic attack. Methoxyl substituent (CH3O) decreases the acidity of nitrogen and oxygen atoms of quinolin-2-one while bromine atom increases acidity of these same sites. These results predict a deprotonation of the nitrogen (N1) of the brominated quinoline-2-ones less energetic than that of the methoxylated derivatives. Conclusively, this work provides data to elucidate the mechanisms to understand the reactivity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one derivatives.},
     year = {2019}
    }
    

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  • TY  - JOUR
    T1  - Theoretical Study of Tautomeric Equilibrium, the Stability, Polarizability, HOMO-LUMO Analysis and Acidity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one Derivatives
    AU  - Lucie Affoue Bede
    AU  - Benjamine Amon Assoma
    AU  - Latyfatou Laye Alao
    AU  - Denis Kicho Yapo
    AU  - Soleymane Kone
    Y1  - 2019/09/11
    PY  - 2019
    N1  - https://doi.org/10.11648/j.ijctc.20190702.11
    DO  - 10.11648/j.ijctc.20190702.11
    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  - 107
    EP  - 114
    PB  - Science Publishing Group
    SN  - 2376-7308
    UR  - https://doi.org/10.11648/j.ijctc.20190702.11
    AB  - Quinoline derivatives have several reactionnels sites conferring them a hight reactivity. This makes them excellent precursors in the synthesis of new bioactive compounds. Considering the interest of quinoline chemistry and diversity of their applications, a study based on a theoretical approach of reactivity of 4,4-dimethyl-3,4-dihydro-quinolin-2(1H)-one and derivatives is carried. This study determines interaction sites of these derivatives in order to understand the mechanisms involved. Calculations are carried in gaseous phase and solution in N, N-dimethylformamide (DMF). Density Functional Theory (DFT/B3LYP) method associated with 6-311G(d) and 6-311+G (d) bases is used to perform these calculations. Results of the thermodynamic parameters showed that there is a tautomeric equilibrium relationship between the different derivatives Reactivity analysis based on Frontier Molecular Orbitals theory revealed that tautomers ketone are less reactive than tautomers enol. Calculation of Fukui indices indicates that the carbon atoms C2, C3, C5, C 7 and C8 of quinoline-2-one ring are sites favorable to nucleophilic attack. Atoms N1, C4, C6 and O11 are nucleophilic sites therefore favorable to an electrophilic attack. Methoxyl substituent (CH3O) decreases the acidity of nitrogen and oxygen atoms of quinolin-2-one while bromine atom increases acidity of these same sites. These results predict a deprotonation of the nitrogen (N1) of the brominated quinoline-2-ones less energetic than that of the methoxylated derivatives. Conclusively, this work provides data to elucidate the mechanisms to understand the reactivity of 4,4-diméthyl-3,4-dihydroquinolin-2(1H)-one derivatives.
    VL  - 7
    IS  - 2
    ER  - 

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

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

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

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

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

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