New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures
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 center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot 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 center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot ...center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.
Source:
Crystal Growth & Design, 2020, 20, 5, 2943-2951Publisher:
- Amer Chemical Soc, Washington
Funding / projects:
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
- Studies of enzyme interactions with toxic and pharmacologically active molecules (RS-172023)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1021/acs.cgd.9b01565
ISSN: 1528-7483
WoS: 000535174000017
Scopus: 2-s2.0-85085149156
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Janjić, Goran AU - Jelić, Stefan AU - Trišović, Nemanja AU - Popović, Dragan AU - Đorđević, Ivana AU - Milčić, Miloš PY - 2020 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4527 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 center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot 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 center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups. PB - Amer Chemical Soc, Washington T2 - Crystal Growth & Design T1 - New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures EP - 2951 IS - 5 SP - 2943 VL - 20 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 center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot 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 center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.", publisher = "Amer Chemical Soc, Washington", journal = "Crystal Growth & Design", title = "New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures", pages = "2951-2943", number = "5", volume = "20", 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 & Design Amer Chemical Soc, Washington., 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 & 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 & Design, 20, no. 5 (2020):2943-2951, https://doi.org/10.1021/acs.cgd.9b01565 . .