Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2-[4-(dimethylamino)phenyl]-1,3-dioxane

The structure of 5,5-bis(bromomethyl)-2-[4-(dimethylamino)phenyl]-1,3-dioxane, a promising reagent for fine organic synthesis and a potential bactericidal compound, was investigated by 1 Н and 13 С NMR spectroscopy and X-ray structural analysis. Both in the crystalline state and in solution, molecules of this compound have a chair conformation with an equatorial orientation of the aromatic substituent. Density functional theory calculations at the PBE/3ξ level of theory were used to determine the pathway of conformational transformations and the potential barriers for internal rotation of aromatic and N(CH 3 ) 2 groups both for the isolated molecule and for a chloroform solution. A conclusion was drawn that the nearest solvation shell of the studied 1,3-dioxane comprises a relatively small (up to four) number of solvent molecules.