Fluorinated rings: conformation and application

R Mondal, M Agbaria, Z Nairoukh - Chemistry–A European …, 2021 - Wiley Online Library
The introduction of fluorine atoms into molecules and materials across many fields of
academic and industrial research is now commonplace, owing to their unique properties. A …

The formation of all-cis-(multi)fluorinated piperidines by a dearomatization–hydrogenation process

Z Nairoukh, M Wollenburg, C Schlepphorst… - Nature …, 2019 - nature.com
Piperidines and fluorine substituents are both independently indispensable components in
pharmaceuticals, agrochemicals and materials. Logically, the incorporation of fluorine atoms …

Accessing (multi) fluorinated piperidines using heterogeneous hydrogenation

T Wagener, A Heusler, Z Nairoukh, K Bergander… - ACS …, 2020 - ACS Publications
Fluorinated piperidines are desirable motifs for pharmaceutical and agrochemical research.
Nevertheless, general synthetic access remains out of reach. Herein, we describe a simple …

pH‐responsive aminoproline‐containing collagen triple helices

J Egli, C Siebler, B Maryasin… - … A European Journal, 2017 - Wiley Online Library
Abstract (4S)‐and (4R)‐configured aminoproline (Amp) residues were used as pH‐
responsive probes to tune the thermal stability of collagen triple helices in acidic and basic …

Understanding the Conformational Behavior of Fluorinated Piperidines: The Origin of the Axial‐F Preference

Z Nairoukh, F Strieth‐Kalthoff… - … A European Journal, 2020 - Wiley Online Library
Gaining an understanding of the conformational behavior of fluorinated compounds would
allow for expansion of the current molecular design toolbox. In order to facilitate drug …

The Conformational Behaviour of Fluorinated Tetrahydrothiopyran

N Egbaria, M Agbaria, VA Borin… - … A European Journal, 2024 - Wiley Online Library
We present a comprehensive study on the conformational behavior of diversely substituted 4‐
fluorotetrahydrothiopyran derivatives. Through quantum chemical simulations including DFT …

Regio-and stereochemical stability induced by anomeric and gauche effects in difluorinated pyrrolidines

AFC Silva, FA Martins… - Beilstein Journal of Organic …, 2024 - beilstein-journals.org
Selective fluorination of the pyrrolidine ring in proline motifs has been found to induce
significant conformational changes that impact the structure and biological roles of modified …

The Role of Intramolecular Interactions on the Bioactive Conformation of Epinephrine

DR Silva, JM Silla, LA Santos… - Molecular …, 2019 - Wiley Online Library
The structure of bioactive compounds inside their biological target is mainly dictated by the
intermolecular interactions present in the binding side, whereas intramolecular interactions …

[HTML][HTML] Conformational analysis of 2, 2-difluoroethylamine hydrochloride: double gauche effect

JM Silla, CJ Duarte, RA Cormanich… - Beilstein journal of …, 2014 - beilstein-journals.org
The gauche effect in fluorinated alkylammonium salts is well known and attributed either to
an intramolecular hydrogen bond or to an electrostatic attraction between the positively …

Interactions affecting 1 JC–F SSCCs in neutral and ionic 2-, 3-and 4-fluoro-substituted piperidines: normal and reverse fluorine Perlin-like effect

JM Silla, MP Freitas - RSC advances, 2016 - pubs.rsc.org
The fluorine Perlin-like effect is an NMR phenomenon characterized by| 1JC–Fax|<| 1JC–
Feq| in fluorinated six-membered rings and can be useful to determine the stereochemistry …