Structure and conformational analysis of 5,5-bis(bromomethyl)-2-trichloromethyl-1,3-dioxane by XRD, NMR and computer simulation

•A new 5,5-bis(bromomethyl)-2-trichloromethyl-1,3-dioxane 1 has been synthesized.•The structure of synthesized compound 1 was characterized by NMR and single crystal XRD study.•Using the DFT approximation PBE/3ζ, an exhaustive conformational analysis of dioxane 1 was carried out in a vacuum and in a chloroform solution (explicit model) with the identification of the route of conformational transformations, including the determination of main and local minima, as well as of transition states between them and barriers to the internal rotation of equatorial and axial CCl3 substituent. According to the NMR 1Н, 13С and X-ray analysis data molecules of 5,5-bis(bromomethyl)-2-trichloromethyl-1,3-dioxane in the crystalline phase and in solution have a chair conformation with an equatorial trichloromethyl group. The route of conformational transformations for isolated molecule and for a cluster with five chloroform molecules, as well as a transition states and barriers to the internal rotation of the axial and equatorial trichloromethyl group have been established using DFT approximation PBE/3ξ. [Display omitted]