Conformational Analysis of 5-Ethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxane

Abstract

Computer simulation of conformational transformations of 5-ethyl-5-hydroxymefhyl-2,2-dimefhyl-1,3-dioxane in the gas phase, as well as in mixtures with chloroform, DMSO, benzene, and water, has been performed at the DFT PBE/3ζ level of theory. The conformational equilibrium involves chair conformers with axial and equatorial hydroxymethyl group and 2,5-twist structure. The chair conformer with equatorial hydroxymethyl group predominates in benzene and DMSO, whereas the major conformer in the gas phase and in chloroform and water is that with axial hydroxymethyl group. The results of calculations were confirmed by the two-dimensional NMR spectra (NOESY) recorded from solutions in DMSO-d₆ and CDCl₃.