A. Dmitrienko, V. Karnoukhova, A. Potemkin
Jun 16, 2017
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Journal
Chemistry of Heterocyclic Compounds
Abstract
We report the synthesis, as well as the molecular and crystal structures of N-(2-halo-2,2-dinitroethyl)pyrrolidine-2,5-diones (Hal = F, Cl, Br). A combination of X-ray structural analysis and quantum chemistry calculations was used for comparative analysis of molecular packing in the crystals of the synthesized compounds. It was shown that the fluorinated derivative contained a shortened F···F halogen bond of the first type, and in the bromo derivative the bromine atoms formed a relatively strong Br···O=C halogen bond of the second type, while the chlorine atom in the structure of chloro derivative interacted with a nitro group oxygen atom, also forming a weak Cl···O2N halogen bond of the second type. These variations in the “preferences” of different halogen atoms resulted in observable differences in the crystal structures of the studied compounds.