Intramolecular hydrogen bonding and conformational preferences on 2-fluoro-phenylaminocyclohexanol

Resumo

The aim of this study is to evaluate the influence and strength of possible intramolecular hydrogen bonding (IntraHB) involving N-H--O, O-H--N, O-H--F and N-H--F molecular moieties as a driving force on the conformational preferences of 2-fluoro-phenylaminocyclohexanol. To achieve our purpose we synthesized the compound and performed it's characterization using Nuclear Magnetic Resonance Spectroscopy (NMR). Quantum mechanical calculations were carried out to evaluate the effect of IntraHB on the conformational stability. Experimental and theoretical results showed that N-H--F and O-H--N IntraHB have a greater influence on the conformacional preferably adopted by the molecule.