Applications of fluorine in medicinal chemistry

EP Gillis, KJ Eastman, MD Hill… - Journal of medicinal …, 2015 - ACS Publications
The role of fluorine in drug design and development is expanding rapidly as we learn more
about the unique properties associated with this unusual element and how to deploy it with …

Organic fluorine as a hydrogen-bond acceptor: recent examples and applications

PA Champagne, J Desroches, JF Paquin - Synthesis, 2015 - thieme-connect.com
For more than three decades, the ability of a fluorine atom involved in a C–F bond to act as a
hydrogen-bond acceptor has been a controversial issue. Throughout the years, more and …

Fluorine substitution tunes the nanofiber chirality of supramolecular hydrogels to promote cell adhesion and proliferation

H Lu, Y Zhao, S Qin, Y Zhang, J Liu, J Zhang… - Advanced Fiber …, 2023 - Springer
Fluorine atoms confer desirable biophysical, chemical, and biological properties to
peptides/proteins by participating in various intermolecular interactions with their …

Mechanism and Origin of the Unexpected Chemoselectivity in Fluorocyclization of o-Styryl Benzamides with a Hypervalent Fluoroiodane Reagent

T Yan, B Zhou, XS Xue, JP Cheng - The Journal of Organic …, 2016 - ACS Publications
The mechanism and origin of the unexpected chemoselectivity in fluorocyclization of o-styryl
benzamide with a cyclic hypervalent fluoroiodane reagent were explored with DFT …

Positioning a Carbon–Fluorine Bond over the π Cloud of an Aromatic Ring: A Different Type of Arene Activation

MG Holl, MD Struble, P Singal… - Angewandte Chemie …, 2016 - Wiley Online Library
It is known that the fluoro group has only a small effect on the rates of electrophilic aromatic
substitutions. Imagine instead a carbon–fluorine (C− F) bond positioned tightly over the π …

Theoretical study of Lewis acid activation models for hypervalent fluoroiodane reagent: The generality of “F-coordination” activation model

B Zhou, X Xue, J Cheng - Tetrahedron Letters, 2017 - Elsevier
The bench-stable cyclic hypervalent fluoroiodane reagent (1) is receiving increasing
attention in fluorine chemistry because of its completely new reactivity. Fluorination …

The pitfalls of using J HF spin–spin coupling constants to infer hydrogen bond formation in organofluorine compounds

G Cariello, LA Zeoly, BA Piscelli, T Lectka… - Chemical …, 2023 - pubs.rsc.org
Theoretical decomposition of “through space” spin–spin coupling constants (SSCCs) in
organofluorine compounds signal that intramolecular hydrogen bonds (H-bonds) are not the …

aromatic triazole foldamers induced by C–H··· X (X= F, Cl) intramolecular hydrogen bonding

J Shang, NM Gallagher, F Bie, Q Li, Y Che… - The Journal of …, 2014 - ACS Publications
Aryl-triazole oligomers based on isobutyl 4-fluorobenzoate and isobutyl 4-chlorobenzoate
were designed and synthesized. Crystal structure and 1H–1H NOESY experiments …

Search for a Strong, Virtually “No‐Shift” Hydrogen Bond: A Cage Molecule with an Exceptional OH⋅⋅⋅ F Interaction

MD Struble, C Kelly, MA Siegler… - Angewandte Chemie, 2014 - Wiley Online Library
Reported herein is the synthesis of a molecule containing an unusually strong hydrogen
bond between an OH donor and a covalent F acceptor, a heretofore somewhat ill‐defined if …

C–H··· F Hydrogen bonds in solid solutions of benzoic acid and 4-fluorobenzoic acid

S Chakraborty, GR Desiraju - Crystal Growth & Design, 2018 - ACS Publications
Solid solutions (SS) of benzoic acid (BA) and 4-fluorobenzoic acid (4FBA) are monitored
with respect to increasing fluorine content. All 10 SS studied take a crystal structure that is …