Developing new derivatives of 3‐X‐4‐hydroxy‐2(1H)‐quinolone as quinoline‐based chemosensors for detecting fluoride: Theoretical study on nucleophilicity and hydrogen‐bonding via various analyses

Thermodynamic and electronic features of new derivatives of 3‐X‐4‐hydroxy‐2(1H)‐quinolone (X = H, OH, OMe, NH2, NMe2, Me, NHMe, F, Cl, CN, CF3, NO2, CCl3, and COH; 1–14) are investigated, at the B3LYP/6‐311++G** level of theory. Structures with electron‐donating groups (EDGs) show higher values of n...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2022-12, Vol.35 (12), p.n/a
Main Author: Mohebi, Nazanin
Format: Article
Language:English
Subjects:
Bonding strength
Charge transfer
Chemical bonds
Chemical sensors
Chemoreceptors
DFT
Dipole moments
fluoride
Fukui function
Hirshfeld
Hydrogen bonding
NCI
Nitrogen dioxide
Quinoline
quinolone
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Summary:Thermodynamic and electronic features of new derivatives of 3‐X‐4‐hydroxy‐2(1H)‐quinolone (X = H, OH, OMe, NH2, NMe2, Me, NHMe, F, Cl, CN, CF3, NO2, CCl3, and COH; 1–14) are investigated, at the B3LYP/6‐311++G** level of theory. Structures with electron‐donating groups (EDGs) show higher values of nucleophilicity (N) than those of electron‐withdrawing groups (EWGs), which are proved via Fukui functions. To determine the sensing ability of 1–14, fluoride (F) as an important industrial, chemical, and biological anion is complexed to the 1–14. All 1–14 establish the strong hydrogen bonding with F, which is verified by various analyses including natural bond orbital (NBO), atoms in molecules (AIM), atomic dipole moment corrected Hirshfeld charges (ADCH), and non‐covalent interaction (NCI). The excitation state study provides the noteworthy results of the charge transfer (CT), natural transition orbital (NTO), and the UV‐Vis spectrum. The obtained outcomes promise new series of quinoline‐based chemosensors (QBCs) to detect F. Thermodynamic and electronic features of new derivatives of 3‐X‐4‐hydroxy‐2(1H)‐quinolone (1–14) are investigated, at the B3LYP/6‐311++G** level of theory. Structures with electron‐donating groups (EDGs) show higher values of nucleophilicity (N) than those of electron‐withdrawing groups (EWGs) proved via Fukui functions. To determine the sensing ability of 1–14, fluoride (F) as an important industrial, chemical, and biological anion is complexed to the 1–14. All 1–14 establish the strong hydrogen bonding with F, which is verified by various analyses.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.4422