On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives
Само за регистроване кориснике
2021
Аутори
Gak Simić, KristinaĐorđević, Ivana S.
Lazić, Anita M.
Radovanović, Lidija D.
Petković-Benazzouz, Marija
Rogan, Jelena R.
Trišović, Nemanja
Janjić, Goran
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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 interactio...n 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.
Кључне речи:
Atoms / Crystal atomic structure / Fluorine / Hydrogen bonds / Molecules / Paraffins / Quantum chemistry / Single crystals / Supramolecular chemistry / Electrostatic potential maps / Intermolecular interactions / Parallel interactions / Quantitative assessments / Quantum chemical studies / Single crystal X-ray crystallography / Supramolecular architectures / Three-dimensional networks / X ray crystallographyИзвор:
CrystEngComm, 2021, 23, 13, 2606-2622Издавач:
- Royal Society of Chemistry
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200135 (Универзитет у Београду, Технолошко-металуршки факултет) (RS-MESTD-inst-2020-200135)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200287 (Иновациони центар Технолошко-металуршког факултета у Београду доо) (RS-MESTD-inst-2020-200287)
- Графитне и неорганске наноструктуре ниске димензионалности (RS-MESTD-Basic Research (BR or ON)-171035)
DOI: 10.1039/d0ce01841d
ISSN: 1466-8033
WoS: 000637138000015
Scopus: 2-s2.0-85103685179
Институција/група
IHTMTY - JOUR AU - Gak Simić, Kristina AU - Đorđević, Ivana S. AU - Lazić, Anita M. AU - Radovanović, Lidija D. AU - Petković-Benazzouz, Marija AU - Rogan, Jelena R. AU - Trišović, Nemanja AU - Janjić, Goran PY - 2021 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4678 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-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. PB - Royal Society of Chemistry T2 - CrystEngComm T1 - On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives VL - 23 IS - 13 SP - 2606 EP - 2622 DO - 10.1039/d0ce01841d ER -
@article{ author = "Gak Simić, Kristina and Đorđević, Ivana S. and Lazić, Anita M. and Radovanović, Lidija D. and Petković-Benazzouz, Marija and Rogan, Jelena R. 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-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.", publisher = "Royal Society of Chemistry", journal = "CrystEngComm", title = "On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives", volume = "23", number = "13", pages = "2606-2622", doi = "10.1039/d0ce01841d" }
Gak Simić, K., Đorđević, I. S., Lazić, A. M., Radovanović, L. D., Petković-Benazzouz, M., Rogan, J. R., Trišović, N.,& Janjić, G.. (2021). On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives. in CrystEngComm Royal Society of Chemistry., 23(13), 2606-2622. https://doi.org/10.1039/d0ce01841d
Gak Simić K, Đorđević IS, Lazić AM, Radovanović LD, Petković-Benazzouz M, Rogan JR, 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 S., Lazić, Anita M., Radovanović, Lidija D., Petković-Benazzouz, Marija, Rogan, Jelena R., 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 . .