Molecular properties of selenomaltols : new interesting ligands for bioactive metal complexes

2015
journal article
article
2
dc.abstract.enProperties 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.affiliationWydział Chemii : Zakład Fizyki Chemicznejpl
dc.contributor.authorTejchman, Waldemarpl
dc.contributor.authorProniewicz, Leonard - 131552 pl
dc.contributor.authorZborowski, Krzysztof - 101661 pl
dc.date.accessioned2015-11-30T07:47:02Z
dc.date.available2015-11-30T07:47:02Z
dc.date.issued2015pl
dc.description.number8pl
dc.description.physical536-541pl
dc.description.volume28pl
dc.identifier.doi10.1002/poc.3443pl
dc.identifier.eissn1099-1395pl
dc.identifier.issn0894-3230pl
dc.identifier.urihttp://ruj.uj.edu.pl/xmlui/handle/item/17261
dc.languageengpl
dc.language.containerengpl
dc.rights.licencebez licencji
dc.subject.enaromaticitypl
dc.subject.enhydroxypyronespl
dc.subject.enheteroaromaticitypl
dc.subject.enmaltolpl
dc.subject.enselenomaltolspl
dc.subtypeArticlepl
dc.titleMolecular properties of selenomaltols : new interesting ligands for bioactive metal complexespl
dc.title.journalJournal of Physical Organic Chemistrypl
dc.typeJournalArticlepl
dspace.entity.typePublication
dc.abstract.enpl
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.affiliationpl
Wydział Chemii : Zakład Fizyki Chemicznej
dc.contributor.authorpl
Tejchman, Waldemar
dc.contributor.authorpl
Proniewicz, Leonard - 131552
dc.contributor.authorpl
Zborowski, Krzysztof - 101661
dc.date.accessioned
2015-11-30T07:47:02Z
dc.date.available
2015-11-30T07:47:02Z
dc.date.issuedpl
2015
dc.description.numberpl
8
dc.description.physicalpl
536-541
dc.description.volumepl
28
dc.identifier.doipl
10.1002/poc.3443
dc.identifier.eissnpl
1099-1395
dc.identifier.issnpl
0894-3230
dc.identifier.uri
http://ruj.uj.edu.pl/xmlui/handle/item/17261
dc.languagepl
eng
dc.language.containerpl
eng
dc.rights.licence
bez licencji
dc.subject.enpl
aromaticity
dc.subject.enpl
hydroxypyrones
dc.subject.enpl
heteroaromaticity
dc.subject.enpl
maltol
dc.subject.enpl
selenomaltols
dc.subtypepl
Article
dc.titlepl
Molecular properties of selenomaltols : new interesting ligands for bioactive metal complexes
dc.title.journalpl
Journal of Physical Organic Chemistry
dc.typepl
JournalArticle
dspace.entity.type
Publication
Affiliations

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