| Popis: |
Properties of numerous selenium derivatives of maltol (3-hydroxy-2-methyl-4H-pyran-4-one), which is an important ligand in medicinal chemistry, were studied. Selenium derivatives were obtained using consecutive in silico replacements of maltol oxygen atoms, which produced three mono-substituted, three di-substituted and one tri-substituted derivatives. The geometry optimisations for these compounds in neutral, anionic and cationic forms were performed at the B1LYP/6-311++G** level of theory. The aromatic properties of the considered selenium compounds were studied in their heterocyclic rings using several indices of aromaticity: harmonic oscillator model of aromaticity, nucleus independent chemical shift(0), nucleus independent chemical shift(1), aromatic stabilisation energy, H index, para delocalisation index and multicentre index. The methods cover all of the main types of aromaticity indices: geometric, magnetic, energetic and electronic. The calculated data show the identical aromaticity order (cation > neutral molecule > anion) for maltol and its thio and seleno derivatives. The predicted aromaticity levels of selenomaltols were compared with the previously studied maltol and various thiomaltols. Copyright © 2015 John Wiley & Sons, Ltd. |
