Abstract
The exo⇔endo isomerization of 2,5-dimethoxybenzaldehyde was theoretically studied by density functional theory (DFT) to examine its favored conformers via sp2–sp2 single rotation. Both isomers were docked against 1BNA DNA to elucidate their binding ability, and the DFT-computed structural parameters results were matched with the X-ray diffraction (XRD) crystallographic parameters. XRD analysis showed that the exo-isomer was structurally favored and was also considered as the kinetically preferred isomer, while several hydrogen-bonding interactions detected in the crystal lattice by XRD were in good agreement with the Hirshfeld surface analysis calculations. The molecular electrostatic potential, Mulliken and natural population analysis charges, frontier molecular orbitals (HOMO/LUMO), and global reactivity descriptors quantum parameters were also determined at the B3LYP/6-311G(d,p) level of theory. The computed electronic calculations, i.e., TD-SCF/DFT, B3LYP-IR, NMR-DB, and GIAO-NMR, were compared to the experimental UV–Vis., optical energy gap, FTIR, and 1H-NMR, respectively. The thermal behavior of 2,5-dimethoxybenzaldehyde was also evaluated in an open atmosphere by a thermogravimetric–derivative thermogravimetric analysis, indicating its stability up to 95 °C.
Highlights
Aldehydes and ketones are key building blocks for a wide range of synthetic and natural derivatives and are used in several applications such as the Schiff base reaction [1,2,3,4]
2,5-Dimethoxybenzaldehyde crystallized in the kinetically favored exo-isomer form (Figure 1a) was monoclinic, with a p21/n space group, and four molecules were crystallized in a packing unit cell (Figure 1b)
The B3LYP/6-311G(d,p)-optimized exo-isomer structure was consistent with the X-ray diffraction (XRD) experimental result of the solid state, as shown in Figure 1c and Table 2
Summary
Aldehydes and ketones are key building blocks for a wide range of synthetic and natural derivatives and are used in several applications such as the Schiff base reaction [1,2,3,4]. Improvements in density functional theory (DFT) methods have allowed the reliable theoretical application of larger molecules with even more 100 atoms in the development of new pharmaceutical agents. Molecular docking is a suitable method for understanding the binding mode of drugs with DNA via, e.g., noncovalent interactions [14,15,16,17,18], and is usually applied for the design of novel drug structures. Both experimental and theoretical docking studies help to explore organic and inorganic complexes as potential drug candidates [18]
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