Experimental
and Theoretical Studies of Intramolecular
Hydrogen Bonding in 3‑Hydroxytetrahydropyran: Beyond AIM Analysis
- Publication date
- Publisher
Abstract
The conformational preferences of
3-hydroxytetrahydropyran (<b>1</b>) were evaluated using infrared
and nuclear magnetic resonance
spectroscopic data in solvents of different polarities. Theoretical
calculations in the isolated phase and including the solvent effect
were performed, showing that the most stable conformations for compound <b>1</b> are those containing the substituent in the axial and equatorial
orientations. The axial conformation is more stable in the isolated
phase and in a nonpolar solvent, while the equatorial conformation
is more stable than the axial in polar media. The occurrence of intramolecular
hydrogen-bonded O–H···O in the axial conformer
was detected from infrared spectra in a nonpolar solvent at different
concentrations. Our attempt to evaluate this interaction using population
natural bond orbital and topological quantum theory of atoms in molecules
analyses failed, but topological noncovalent interaction analysis
was capable of characterizing it