Excited state aromatization assisted push-pull abilities of two unsaturated oxazolone derivatives
Joint Authors
Sevincek, Resul
Karabıyık, Hasan
Urut, Gulsiye Ozturk
Source
Journal of Saudi Chemical Society
Issue
Vol. 22, Issue 5 (31 Jul. 2018), pp.519-526, 8 p.
Publisher
Publication Date
2018-07-31
Country of Publication
Saudi Arabia
No. of Pages
8
Main Subjects
Abstract EN
Molecular structures of two unsaturated oxazolone derivatives involving furan rings, which are decorated with p-tolyl (FurM) and 4-nitro phenyl (FurN), were investigated by X-ray crystallography and quantum chemical calculations.
Their ground and excited states were examined by DFT and TD-DFT computations with the aid of topological electron density studies, NBO and Charge Decomposition Analysis.
Both compounds have push-pull (D–p–A) framework using oxazolone ring as p-linker.
Depending on the transitions from the ground to excited states, intramolecular charge transfer (ICT) in both compounds results in aromatization of oxazolones.
Push-pull ability of FurN has more pronounced than that of FurM.
The use of furan instead of almost fully aromatic benzenoid ring reduces HOMO_LUMO band gap due to relatively low aromaticity level of furan.
Introduction of nitro substituent leads to a further reduction in HOMO_LUMO gap.
In addition, electronic redistribution in the excited state results in aromatization of oxazolone moieties without elongation of carbonyl bonds.
American Psychological Association (APA)
Sevincek, Resul& Karabıyık, Hasan& Urut, Gulsiye Ozturk. 2018. Excited state aromatization assisted push-pull abilities of two unsaturated oxazolone derivatives. Journal of Saudi Chemical Society،Vol. 22, no. 5, pp.519-526.
https://search.emarefa.net/detail/BIM-836343
Modern Language Association (MLA)
Sevincek, Resul…[et al.]. Excited state aromatization assisted push-pull abilities of two unsaturated oxazolone derivatives. Journal of Saudi Chemical Society Vol. 22, no. 5 (Jul. 2018), pp.519-526.
https://search.emarefa.net/detail/BIM-836343
American Medical Association (AMA)
Sevincek, Resul& Karabıyık, Hasan& Urut, Gulsiye Ozturk. Excited state aromatization assisted push-pull abilities of two unsaturated oxazolone derivatives. Journal of Saudi Chemical Society. 2018. Vol. 22, no. 5, pp.519-526.
https://search.emarefa.net/detail/BIM-836343
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references : p. 526
Record ID
BIM-836343