New Theoretical Insight into Fluorination and Fluorine–Fluorine Interactions as a Driving Force in Crystal Structures
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2020
Article (Published version)

American Chemical Society
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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
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