TD-DFT calculations, dipole moments, and solvatochromic properties of 2-aminochromone-3-carboxaldehyde and its hydrazone derivatives

2-Aminochromone-3-carboxaldehyde ( ACC ) and its hydrazones ( ACMHCA and ACMNPHTCA ) with semicarbazide hydrochloride and N -phenylthiosemicarbazide were synthesized and characterized by elemental analysis and spectral studies. The solvatochromic behavior of the title compounds in various solvents s...

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Bibliographic Details
Published in:RSC advances 2023-09, Vol.13 (38), p.26587-2663
Main Authors: Adly, Omima M. I, Taha, Ali, Fahmy, Shery A, Ibrahim, Magdy A
Format: Article
Language:English
Subjects:
Biological activity
Charge transfer
Chemical equilibrium
Chemistry
Dipole moments
Hydrazones
Mathematical analysis
Molecular orbitals
NMR
Nuclear magnetic resonance
Solvents
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Summary:2-Aminochromone-3-carboxaldehyde ( ACC ) and its hydrazones ( ACMHCA and ACMNPHTCA ) with semicarbazide hydrochloride and N -phenylthiosemicarbazide were synthesized and characterized by elemental analysis and spectral studies. The solvatochromic behavior of the title compounds in various solvents showed distinct bathochromic shifts on going from nonpolar to polar solvents, suggesting intramolecular-charge-transfer (ICT) solute-solvent interactions. The ground and excited state dipole moments of ACC , ACMHCA , and ACMNPHTCA were determined experimentally by the solvatochromic shift method using the Bilot-Kawski, Lippert-Mataga, Bakhshiev, Kawski-Chamma-Viallet functions, and a microscopic Reichardt's solvent polarity parameter ( E N T ). All the investigated molecules showed a substantial increase in the dipole moment upon excitation to the emitting state. The experimental results were generally consistent with the values obtained by the TD-DFT, B3LYP/6-311G++(d,p) method. Molecular electrostatic potential (MEP) mapping and natural charge and natural bonding orbital (NBO) analysis were performed and the results were discussed. The 1 H NMR chemical shifts of the prepared compounds were simulated by the gage independent atomic orbital (GIAO) method and compared with their experimental chemical shift values. The biological activity data were correlated with the frontier molecular orbitals. The photovoltaic behavior of the title compounds showed there was sufficient electron injection. 2-Aminochromone-3-carboxaldehyde ( ACC ) and its hydrazones ( ACMHCA and ACMNPHTCA ) with semicarbazide hydrochloride and N -phenylthiosemicarbazide were synthesized and characterized by elemental analysis and spectral studies.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra05081e