Binding properties of aromatic carbon-bound fluorine
Andrew V Razgulin1, Sandro Mecozzi
1Department of Chemistry and School of Pharmacy, University of Wisconsin, 777 Highland Avenue, Madison, WI 53705, USA.
Journal of Medicinal Chemistry
|December 22, 2006
Summary
Aromatic fluorine atoms can form significant hydrogen bonds and interact with charged molecules, according to computational analysis. This finding is crucial for understanding molecular interactions in medicinal chemistry.
Area of Science:
- Computational chemistry
- Medicinal chemistry
- Molecular interactions
Background:
- Aromatic carbon-bound fluorine is prevalent in medicinal chemistry.
- Understanding fluorine's role in molecular interactions is key for drug design.
Purpose of the Study:
- To computationally analyze the hydrogen bonding and electrostatic interaction capabilities of aromatic fluorine.
- To quantify these interactions with water and cations.
Main Methods:
- Systematic computational analysis using Hartree-Fock (HF), Møller–Plesset (MP2), and Density Functional Theory (DFT) levels of theory.
- Calculation of interaction energies between common fluoroaromatics, water, and cations.
Main Results:
- Aromatic fluorine atoms can participate in significant hydrogen bonds.
- Aromatic fluorine exhibits notable electrostatic interactions with cations.
- The strength of these interactions is dependent on the level of theory used.
Conclusions:
- Aromatic fluorine is an important functional group for molecular recognition through hydrogen bonding and electrostatic interactions.
- These findings have implications for the design of novel pharmaceuticals and understanding biological interactions.
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