On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives
Samo za registrovane korisnike
2021
Autori
Gak Simić, KristinaĐorđević, Ivana
Lazić, Anita
Radovanović, Lidija
Petković-Benazzouz, Marija
Rogan, Jelena
Trišović, Nemanja
Janjić, Goran
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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-HMIDLINE HORIZONTAL ELLIPSISO, C-HMIDLINE HORIZONTAL ELLIPSIS pi, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HMIDLINE HORIZONTAL ELLIPSISF interaction in the case of 2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FMIDLINE HORIZONTAL ELLIPSISF interaction in the crystal structure of 2 results 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 FMIDLINE HORIZONTAL ELLIPSISF interaction is absent.
Izvor:
CrystEngComm, 2021, 23, 13, 2606-2622Finansiranje / projekti:
- Grafitne i neorganske nanostrukture niske dimenzionalnosti (RS-MESTD-Basic Research (BR or ON)-171035)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200026 (Univerzitet u Beogradu, Institut za hemiju, tehnologiju i metalurgiju - IHTM) (RS-MESTD-inst-2020-200026)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200135 (Univerzitet u Beogradu, Tehnološko-metalurški fakultet) (RS-MESTD-inst-2020-200135)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200287 (Inovacioni centar Tehnološko-metalurškog fakulteta u Beogradu doo) (RS-MESTD-inst-2020-200287)
DOI: 10.1039/d0ce01841d
ISSN: 1466-8033
WoS: 000637138000015
Scopus: 2-s2.0-85103685179
Kolekcije
Institucija/grupa
Inovacioni centarTY - JOUR AU - Gak Simić, Kristina AU - Đorđević, Ivana AU - Lazić, Anita AU - Radovanović, Lidija AU - Petković-Benazzouz, Marija AU - Rogan, Jelena AU - Trišović, Nemanja AU - Janjić, Goran PY - 2021 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4888 AB - 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-HMIDLINE HORIZONTAL ELLIPSISO, C-HMIDLINE HORIZONTAL ELLIPSIS pi, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HMIDLINE HORIZONTAL ELLIPSISF interaction in the case of 2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FMIDLINE HORIZONTAL ELLIPSISF interaction in the crystal structure of 2 results 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 FMIDLINE HORIZONTAL ELLIPSISF interaction is absent. T2 - CrystEngComm T1 - On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives EP - 2622 IS - 13 SP - 2606 VL - 23 DO - 10.1039/d0ce01841d ER -
@article{ author = "Gak Simić, Kristina and Đorđević, Ivana and Lazić, Anita and Radovanović, Lidija and Petković-Benazzouz, Marija and Rogan, Jelena and Trišović, Nemanja and Janjić, Goran", year = "2021", 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-HMIDLINE HORIZONTAL ELLIPSISO, C-HMIDLINE HORIZONTAL ELLIPSIS pi, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HMIDLINE HORIZONTAL ELLIPSISF interaction in the case of 2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FMIDLINE HORIZONTAL ELLIPSISF interaction in the crystal structure of 2 results 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 FMIDLINE HORIZONTAL ELLIPSISF interaction is absent.", journal = "CrystEngComm", title = "On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives", pages = "2622-2606", number = "13", volume = "23", doi = "10.1039/d0ce01841d" }
Gak Simić, K., Đorđević, I., Lazić, A., Radovanović, L., Petković-Benazzouz, M., Rogan, J., Trišović, N.,& Janjić, G.. (2021). On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives. in CrystEngComm, 23(13), 2606-2622. https://doi.org/10.1039/d0ce01841d
Gak Simić K, Đorđević I, Lazić A, Radovanović L, Petković-Benazzouz M, Rogan J, Trišović N, Janjić G. On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives. in CrystEngComm. 2021;23(13):2606-2622. doi:10.1039/d0ce01841d .
Gak Simić, Kristina, Đorđević, Ivana, Lazić, Anita, Radovanović, Lidija, Petković-Benazzouz, Marija, Rogan, Jelena, Trišović, Nemanja, Janjić, Goran, "On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives" in CrystEngComm, 23, no. 13 (2021):2606-2622, https://doi.org/10.1039/d0ce01841d . .