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Binding Properties of Aromatic Carbon-Bound Fluorine

2006; American Chemical Society; Volume: 49; Issue: 26 Linguagem: Inglês

10.1021/jm0600702

1520-4804

Andrew V. Razgulin, Sandro Mecozzi,

Synthesis and Reactions of Organic Compounds

A systematic computational analysis of the ability of aromatic carbon-bound fluorine to participate in hydrogen bonding and electrostatic interactions has been completed. The interaction energies between the most common fluoroaromatics used in medicinal chemistry and both water, the prototypical hydrogen bond donor, and several cations have been calculated at different levels of theory (HF, MP2, DFT). Our results show that aromatic fluorine can participate in significant hydrogen bonds and can also interact with charged molecules.