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

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dc.title Esters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling en Hęclik, Karol Szyszkowska, Agnieszka Trzybiński, Damian Woźniak, Krzysztof Klásek, Antonín Zarzyka, Iwona
dc.relation.ispartof Journal of Molecular Modeling
dc.identifier.issn 1610-2940 OCLC, Ulrich, Sherpa/RoMEO, JCR 2017
utb.relation.volume 23
utb.relation.issue 4
dc.event.title 7th Conference on Modeling and Design of Molecular Materials (MDMM)
dc.event.location Trzebnica
utb.event.state-en Poland
utb.event.state-cs Polsko
dc.event.sdate 2016
dc.event.edate 2016
dc.type article
dc.language.iso en
dc.publisher Springer
dc.identifier.doi 10.1007/s00894-017-3284-1
dc.subject Ester en
dc.subject Imidazo[1,5-c]quinazoline ring en
dc.subject Quantum-mechanical modeling en
dc.subject Spectral characterization en
dc.description.abstract 1-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 13C-NMR, 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 quantum-mechanical 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. © 2017, The Author(s). en
utb.faculty Faculty of Technology
utb.identifier.obdid 43877036
utb.identifier.scopus 2-s2.0-85014990690
utb.identifier.wok 000396842700009
utb.identifier.pubmed 28275905
utb.identifier.coden JMMOF
utb.source j-scopus 2017-07-25T08:54:56Z 2017-07-25T08:54:56Z
dc.description.sponsorship IGA/FT/2016/004, UTB, Univerzita Tomáše Bati ve Zlíně
dc.description.sponsorship Interdisciplinary Centre for Mathematical and Computational Modelling in Warsaw [G49-12]; TBU in Zlin [IGA/FT/20017/005]
dc.rights Attribution 4.0 International
dc.rights.access openAccess
utb.contributor.internalauthor Klásek, Antonín
utb.fulltext.affiliation K. Hęclik 1,* & A. Szyszkowska 1 & D. Trzybiński 2 & K. Woźniak 2 & A. Klasek 3 & I. Zarzyka 1 * 1 Department of Chemistry, The University of Technology, Powstańców Warszawy 6, 35-959 Rzeszow, Poland 2 Department of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland 3 Faculty of Technology, Department of Chemistry, Tomas Bata University in Zlin, CZ-762 72 Zlin, Czech Republic
utb.fulltext.dates Received: 1 November 2016 / Accepted: 13 February 2017 / Published online: 8 March 2017
utb.fulltext.sponsorship NMR spectra was made in the Laboratory of Spectrometry, Faculty of Chemistry, Rzeszow University of Technology and was financed from DS budget. The authors would like to thank Interdisciplinary Centre for Mathematical and Computational Modelling in Warsaw for providing computer facilities for possibility of performing of the quantum- mechanical calculations under grant G49-12. Antonín Klásek thanks the financial support from the internal grant of TBU in Zlín (No. IGA/FT/20017/005), funded from the resources of specific university research. Authors thank Hana Gerzova (Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, CZ-762 72 Zlin, Czech Republic) for help in synthesis of 2,6-bis(ethoxycarbonylmethyl)-1-phenylimidazo[1,5-c]quinazoline-3,5-dione.
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