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Molecular properties of selenomaltols : new interesting ligands for bioactive metal complexes
aromaticity
hydroxypyrones
heteroaromaticity
maltol
selenomaltols
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.
dc.abstract.en | 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. | pl |
dc.affiliation | Wydział Chemii : Zakład Fizyki Chemicznej | pl |
dc.contributor.author | Tejchman, Waldemar | pl |
dc.contributor.author | Proniewicz, Leonard - 131552 | pl |
dc.contributor.author | Zborowski, Krzysztof - 101661 | pl |
dc.date.accessioned | 2015-11-30T07:47:02Z | |
dc.date.available | 2015-11-30T07:47:02Z | |
dc.date.issued | 2015 | pl |
dc.description.number | 8 | pl |
dc.description.physical | 536-541 | pl |
dc.description.volume | 28 | pl |
dc.identifier.doi | 10.1002/poc.3443 | pl |
dc.identifier.eissn | 1099-1395 | pl |
dc.identifier.issn | 0894-3230 | pl |
dc.identifier.uri | http://ruj.uj.edu.pl/xmlui/handle/item/17261 | |
dc.language | eng | pl |
dc.language.container | eng | pl |
dc.rights.licence | bez licencji | |
dc.subject.en | aromaticity | pl |
dc.subject.en | hydroxypyrones | pl |
dc.subject.en | heteroaromaticity | pl |
dc.subject.en | maltol | pl |
dc.subject.en | selenomaltols | pl |
dc.subtype | Article | pl |
dc.title | Molecular properties of selenomaltols : new interesting ligands for bioactive metal complexes | pl |
dc.title.journal | Journal of Physical Organic Chemistry | pl |
dc.type | JournalArticle | pl |
dspace.entity.type | Publication |