Fluorination as a Driving Force in Crystal Structures
Конференцијски прилог (Објављена верзија)
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The results of the crystallographic analysis in combination with quantum chemical calculations have shown that fluorination of organic compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of the groups in their neighbourhood. The establishment of F∙∙∙F interactions causes the electron density to shift towards the area of F∙∙∙F contact, thus creating a new region with a higher negative potential and the more pronounced accepting ability. This new region has a larger surface area and it is able to form simultaneous interactions with species from the crystal environment. This compensates the reduction of the accepting capacity of the groups in the neigbourhood of the interacting F atoms. Taking into account the formation of this new region, not only the abundance of F∙∙∙F interactions in the crystal structures (the second largest group of interactions), but also a large number of structures with F∙∙∙O interactions (third largest group... of interactions) can be explained. Only the C–H∙∙∙F interactions are more numerous than F∙∙∙F interactions, indicating an increased affinity of fluorinated compounds for non-polar groups.
Кључне речи:
crystallography / computational chemistry / fluorine / non-covalent interactionsИзвор:
2020Издавач:
- Commission on Quantum Crystallography of IUCr
Институција/група
Institut za multidisciplinarna istraživanjaTY - CONF AU - Trišović, Nemanja AU - Jelić, Stefan AU - Popović, Dragan AU - Đorđević, Ivana AU - Milčić, Miloš AU - Janjić, Goran PY - 2020 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/3055 AB - The results of the crystallographic analysis in combination with quantum chemical calculations have shown that fluorination of organic compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of the groups in their neighbourhood. The establishment of F∙∙∙F interactions causes the electron density to shift towards the area of F∙∙∙F contact, thus creating a new region with a higher negative potential and the more pronounced accepting ability. This new region has a larger surface area and it is able to form simultaneous interactions with species from the crystal environment. This compensates the reduction of the accepting capacity of the groups in the neigbourhood of the interacting F atoms. Taking into account the formation of this new region, not only the abundance of F∙∙∙F interactions in the crystal structures (the second largest group of interactions), but also a large number of structures with F∙∙∙O interactions (third largest group of interactions) can be explained. Only the C–H∙∙∙F interactions are more numerous than F∙∙∙F interactions, indicating an increased affinity of fluorinated compounds for non-polar groups. PB - Commission on Quantum Crystallography of IUCr T1 - Fluorination as a Driving Force in Crystal Structures UR - https://hdl.handle.net/21.15107/rcub_rimsi_3055 ER -
@conference{ author = "Trišović, Nemanja and Jelić, Stefan and Popović, Dragan and Đorđević, Ivana and Milčić, Miloš and Janjić, Goran", year = "2020", abstract = "The results of the crystallographic analysis in combination with quantum chemical calculations have shown that fluorination of organic compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of the groups in their neighbourhood. The establishment of F∙∙∙F interactions causes the electron density to shift towards the area of F∙∙∙F contact, thus creating a new region with a higher negative potential and the more pronounced accepting ability. This new region has a larger surface area and it is able to form simultaneous interactions with species from the crystal environment. This compensates the reduction of the accepting capacity of the groups in the neigbourhood of the interacting F atoms. Taking into account the formation of this new region, not only the abundance of F∙∙∙F interactions in the crystal structures (the second largest group of interactions), but also a large number of structures with F∙∙∙O interactions (third largest group of interactions) can be explained. Only the C–H∙∙∙F interactions are more numerous than F∙∙∙F interactions, indicating an increased affinity of fluorinated compounds for non-polar groups.", publisher = "Commission on Quantum Crystallography of IUCr", title = "Fluorination as a Driving Force in Crystal Structures", url = "https://hdl.handle.net/21.15107/rcub_rimsi_3055" }
Trišović, N., Jelić, S., Popović, D., Đorđević, I., Milčić, M.,& Janjić, G.. (2020). Fluorination as a Driving Force in Crystal Structures. Commission on Quantum Crystallography of IUCr.. https://hdl.handle.net/21.15107/rcub_rimsi_3055
Trišović N, Jelić S, Popović D, Đorđević I, Milčić M, Janjić G. Fluorination as a Driving Force in Crystal Structures. 2020;. https://hdl.handle.net/21.15107/rcub_rimsi_3055 .
Trišović, Nemanja, Jelić, Stefan, Popović, Dragan, Đorđević, Ivana, Milčić, Miloš, Janjić, Goran, "Fluorination as a Driving Force in Crystal Structures" (2020), https://hdl.handle.net/21.15107/rcub_rimsi_3055 .