Artykuł w czasopiśmie
Brak miniatury
Licencja
CC-BYCC-BY - Uznanie autorstwa
 

Esters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling

Uproszczony widok
cris.lastimport.scopus2024-02-12T20:12:33Z
dc.abstract.en1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione reacts with ethyl bromoacetate under mild conditions to give 2-(ethoxycarbonylmethyl)-1-phenyl-6H-imidazo[1,5-c]quinazoline-3,5-dione (MEPIQ) and next 2,6- bis(ethoxycarbonylmethyl)-1-phenylimidazo[1,5- c]quinazoline-3,5-dione (BEPIQ). The products were isolated at high yield and identified on the basis of IR, 1H- and 13CNMR, UV spectroscopy, and X-ray crystallography. Diester (BEPIQ) can be presented by 16 possible pair of enantiomers. Only one pair of them is the most stable and crystallizes which is shown crystallographic research. Based on quantummechanical modeling, with the use of DFT method, which conformers of mono- and diester and why they were formed was explained. It was calculated that 99.93% of the monoester (MEPIQ) is formed at position No. 2 and one pair of the monoester conformers, from six possible, has the largest share (51.63%). These results afforded to limit the number of diester conformers to eight. Unfortunately, the quantum-mechanical calculations performed that their shares are similar. Further quantum-mechanical modeling showed that conformers are able to undergo mutual transformations. As a result only one pair of diester conformers forms crystals. These conformers have substituents in trans position and these substituents are located parallel to imidazoquinazoline ring. This allows for the denser packing of the molecules in the unit cell.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorKlasek, Antonin
dc.contributor.authorZarzyka, Iwona
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorHęclik, Karol
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorSzyszkowska, Agnieszka
dc.date.accessioned2024-01-24T23:20:48Z
dc.date.available2024-01-24T23:20:48Z
dc.date.copyright2017-03-08
dc.date.issued2017
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number4
dc.description.versionFINAL_PUBLISHED
dc.description.volume23
dc.identifier.doi10.1007/S00894-017-3284-1
dc.identifier.issn1610-2940
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/106394
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Molecular Modeling
dc.relation.pagesart.no. 107
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enEster
dc.subject.enImidazo[1,5-c]quinazoline ring
dc.subject.enQuantum-mechanical modeling
dc.subject.enSpectral characterization
dc.titleEsters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling
dc.typeJournalArticle
dspace.entity.typePublication