A comparative study of X-ray structural analysis, DFT computations, and Hirshfeld surface analysis for decahydroacridine-1,8-diones

Hosseininasab, Fatemeh S.; Memarian, Hamid R.; Rudbari, Hadi Amiri; Blacque, Olivier

doi:10.1007/s13738-024-03045-3

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2024

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Cited by 2 publications

References 64 publications

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Weak halogen and hydrogen bonds in three closely related acridine-1,8(2H,5H)-dione derivatives: experimental and computational exploration

Gudimetla,

Kumari,

Ganesan

et al. 2024

Journal of Molecular Structure

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Weak halogen and hydrogen bonds in three closely related acridine-1,8(2H,5H)-dione derivatives: experimental and computational exploration

Gudimetla,

Kumari,

Ganesan

et al. 2024

Journal of Molecular Structure

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Effect of the heterocyclic ring-fusion on the photochemical reactivity of 1,4- dihydropyridines, polyhydroquinolines, and decahydroacridine-1,8-diones

Hosseininasab,

Memarian,

Asgari

2024

Preprint

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Photo-oxidation of 1,4-dihydropyridine, polyhydroquinoline, and decahydroacridine-1,8-dione derivatives was investigated by exposing them to the UV light to elucidate the extent of the ring-fusion and the impact of molecular rigidity on the photo-oxidation completion time. The results indicated that the extent of the ring-fusion affects the time of irradiation, which is mostly due to the rigidity of the heterocyclic ring core regarding the freedom of rotation of the attached CO-groups and the effective delocalization of the nitrogen lone pair towards the attached conjugated part. Furthermore, the results showed the impact of the steric and electronic effects of the C-aryl substitution on the rate of the photo-oxidation. Among these three series of compounds, decahydroacridine-1,8-diones, and 1,4-dihydropyridines have the largest and lowest rate of the photo-oxidation, respectively. The geometry of the considered heterocyclic compounds and their corresponding photo-oxidation intermediates was optimized using the density functional theory (DFT) B3LYP method with 6-311 + + G(d,p) basis set. Computational results explained that the deviations of the N1- and C4-atoms of the dihydropyridine ring core from the ring boat plane can affect the rate of the photoreaction of these three series of compounds. These deviations are dependent on the preferred orientation of the CO group towards the heterocyclic ring, the rigidity of the molecule, and the type, position, and electronic nature of the additional substituent on the aryl ring. The dihedral angle scanning clarified the intramolecular interaction of unbounded atoms in the molecules besides the extent of the electron delocalization on the total energy content of the molecules.

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A comparative study of X-ray structural analysis, DFT computations, and Hirshfeld surface analysis for decahydroacridine-1,8-diones

Cited by 2 publications

References 64 publications

Weak halogen and hydrogen bonds in three closely related acridine-1,8(2H,5H)-dione derivatives: experimental and computational exploration

Weak halogen and hydrogen bonds in three closely related acridine-1,8(2H,5H)-dione derivatives: experimental and computational exploration

Effect of the heterocyclic ring-fusion on the photochemical reactivity of 1,4- dihydropyridines, polyhydroquinolines, and decahydroacridine-1,8-diones

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