New Theoretical Insight into Fluorination and Fluorine–Fluorine Interactions as a Driving Force in Crystal Structures
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2020
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American Chemical Society (ACS)
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Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F···F interactions is followed by the shift of the electron density in the area of F···F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F···F interactions in crystal structures, but also a large number of structures with F···O interactions. Only C–H···F interactions are more numerous than F···F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.
Keywords:
Fluorination / Fluorine–Fluorine Interactions / Crystal StructuresSource:
Crystal Growth and Design, 2020, 20, 5, 2943-2951Publisher:
- American Chemical Society (ACS)
Funding / projects:
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- Studies of enzyme interactions with toxic and pharmacologically active molecules (RS-172023)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
DOI: 10.1021/acs.cgd.9b01565
ISSN: 1528-7483
WoS: 000535174000017
Scopus: 2-s2.0-85085149156
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IHTMTY - JOUR AU - Janjić, Goran AU - Jelić, Stefan AU - Trišović, Nemanja AU - Popović, Dragan AU - Đorđević, Ivana AU - Milčić, Miloš PY - 2020 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3882 AB - Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F···F interactions is followed by the shift of the electron density in the area of F···F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F···F interactions in crystal structures, but also a large number of structures with F···O interactions. Only C–H···F interactions are more numerous than F···F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups. PB - American Chemical Society (ACS) T2 - Crystal Growth and Design T1 - New Theoretical Insight into Fluorination and Fluorine–Fluorine Interactions as a Driving Force in Crystal Structures VL - 20 IS - 5 SP - 2943 EP - 2951 DO - 10.1021/acs.cgd.9b01565 ER -
@article{ author = "Janjić, Goran and Jelić, Stefan and Trišović, Nemanja and Popović, Dragan and Đorđević, Ivana and Milčić, Miloš", year = "2020", abstract = "Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F···F interactions is followed by the shift of the electron density in the area of F···F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F···F interactions in crystal structures, but also a large number of structures with F···O interactions. Only C–H···F interactions are more numerous than F···F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.", publisher = "American Chemical Society (ACS)", journal = "Crystal Growth and Design", title = "New Theoretical Insight into Fluorination and Fluorine–Fluorine Interactions as a Driving Force in Crystal Structures", volume = "20", number = "5", pages = "2943-2951", doi = "10.1021/acs.cgd.9b01565" }
Janjić, G., Jelić, S., Trišović, N., Popović, D., Đorđević, I.,& Milčić, M.. (2020). New Theoretical Insight into Fluorination and Fluorine–Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth and Design American Chemical Society (ACS)., 20(5), 2943-2951. https://doi.org/10.1021/acs.cgd.9b01565
Janjić G, Jelić S, Trišović N, Popović D, Đorđević I, Milčić M. New Theoretical Insight into Fluorination and Fluorine–Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth and Design. 2020;20(5):2943-2951. doi:10.1021/acs.cgd.9b01565 .
Janjić, Goran, Jelić, Stefan, Trišović, Nemanja, Popović, Dragan, Đorđević, Ivana, Milčić, Miloš, "New Theoretical Insight into Fluorination and Fluorine–Fluorine Interactions as a Driving Force in Crystal Structures" in Crystal Growth and Design, 20, no. 5 (2020):2943-2951, https://doi.org/10.1021/acs.cgd.9b01565 . .
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