Abstract
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 1Н and 13С 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(CH3)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.
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ACKNOWLEDGMENTS
The structural study of dioxane 1 was performed at the Agidel Center for Collective Use, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences.
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 8, pp. 1146–1153 https://doi.org/10.31857/S051474922108005X.
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Khazhiev, S.Y., Khusainov, M.A., Khalikov, R.A. et al. Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2-[4-(dimethylamino)phenyl]-1,3-dioxane. Russ J Org Chem 57, 1268–1274 (2021). https://doi.org/10.1134/S1070428021080054
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DOI: https://doi.org/10.1134/S1070428021080054