Structure and Conformational Analysis of 5,5-Bis(bromomethyl)- 2-(4-chlorophenyl)-2-methyl-1,3-dioxane

The structure of 5,5-bis(bromomethyl)-2-(4-chlorophenyl)-2-methyl-1,3-dioxane was studied by 1 H and 13 C NMR spectroscopy and X-ray analysis. The compound was found to exist in crystal and solution as a chair conformer with the axial aromatic substituent. The conformational transformation pathway and potential energy barriers to internal rotation of the aromatic substituent for the isolated molecule and solutions in chloroform and benzene (cluster model) were determined by DFT calculations using PBE functional and 3ξ and def2-SVP basis sets.