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On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives
dc.creator | Gak Simić, Kristina | |
dc.creator | Đorđević, Ivana S. | |
dc.creator | Lazić, Anita M. | |
dc.creator | Radovanović, Lidija D. | |
dc.creator | Petković-Benazzouz, Marija | |
dc.creator | Rogan, Jelena R. | |
dc.creator | Trišović, Nemanja | |
dc.creator | Janjić, Goran | |
dc.date.accessioned | 2021-06-02T08:16:54Z | |
dc.date.available | 2021-06-02T08:16:54Z | |
dc.date.issued | 2021 | |
dc.identifier.issn | 1466-8033 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/4678 | |
dc.description.abstract | The quantitative assessment of intermolecular interactions and their cooperative effects has been performed in spirohydantoin-based model compounds, 3-benzoyl-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-fluorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), through single crystal X-ray crystallography and quantum chemical studies. In both crystal structures, molecules generate the same hydrogen-bonded centrosymmetric R22(8) synthon. The extended supramolecular architectures depend on the C-HO, C-Hπ, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HF interaction in the case of2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FF interaction in the crystal structure of2results in a new region with a larger surface area and a higher negative potential in comparison to the individual fluorine atoms. Establishment of this interaction leads to strengthening of the interaction of one of the fluorine atoms with a third molecule from the environment which does not interact with both of them. When this third molecule interacts with both fluorine atoms simultaneously, the calculations have shown that the effect of strengthening of the individual interactions due to formation of the FF interaction is absent. | sr |
dc.language.iso | en | sr |
dc.publisher | Royal Society of Chemistry | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200026/RS// | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200135/RS// | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200287/RS// | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/171035/RS// | sr |
dc.rights | restrictedAccess | sr |
dc.source | CrystEngComm | sr |
dc.subject | Atoms | sr |
dc.subject | Crystal atomic structure | sr |
dc.subject | Fluorine | sr |
dc.subject | Hydrogen bonds | sr |
dc.subject | Molecules | sr |
dc.subject | Paraffins | sr |
dc.subject | Quantum chemistry | sr |
dc.subject | Single crystals | sr |
dc.subject | Supramolecular chemistry | sr |
dc.subject | Electrostatic potential maps | sr |
dc.subject | Intermolecular interactions | sr |
dc.subject | Parallel interactions | sr |
dc.subject | Quantitative assessments | sr |
dc.subject | Quantum chemical studies | sr |
dc.subject | Single crystal X-ray crystallography | sr |
dc.subject | Supramolecular architectures | sr |
dc.subject | Three-dimensional networks | sr |
dc.subject | X ray crystallography | sr |
dc.title | On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives | sr |
dc.type | article | sr |
dc.rights.license | ARR | sr |
dcterms.abstract | Јањић, Горан В.; Гак Симић, Кристина; Ђорђевић, Ивана С.; Лазић, Aнита М.; Радовановић, Лидија Д.; Петковић-Беназзоуз, Марија; Роган, Јелена Р.; Тришовић, Немања П.; | |
dc.citation.volume | 23 | |
dc.citation.issue | 13 | |
dc.citation.spage | 2606 | |
dc.citation.epage | 2622 | |
dc.citation.rank | M21~ | |
dc.identifier.doi | 10.1039/d0ce01841d | |
dc.identifier.scopus | 2-s2.0-85103685179 | |
dc.identifier.wos | 000637138000015 | |
dc.type.version | publishedVersion | sr |