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

Abstract

Thermodynamic and electronic features of new derivatives of 3-X-4-hydroxy-2 (1H)-quinolone (X = H, OH, OMe, NH 2 , NMe 2 , Me, NHMe, F, Cl, CN, CF 3 , NO 2 , CCl 3 , 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.

Endoplasmic Reticulum-Targeting Quinazolinone-Based Lipophilic Probe for Specific Photoinduced Ferroptosis and Its Induced Lipid Dynamic Regulation

“…Conversely, the quinazolinone–pyridine conjugate becomes more electron-deficient through coordination with the BF 2 group, , which may be a good hydrogen bond receptor for forming hydrogen bonding with water. To understand the hydrogen bond receptor properties of BODIQPy-TPA , atomic dipole moment-corrected Hirshfeld (ADCH) atomic charges were used to calculate the electronegativity of atoms . Using density functional theory (DFT) calculations and wave function analysis, the ADCH charges of oxygen and nitrogen atoms in the quinazolinone moiety of QPy-TPA were found to be −0.4136 and −0.3058, respectively, and those in the quinazolinone moiety of BODIQPy-TPA were −0.4152 and −0.3458, respectively (Figure and Tables S1, S2).…”