@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://article.sciencepublishinggroup.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}
}

Copy | Download

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  - 

Copy | Download