Adducts of 2-Pyridylselenenyl Halides and Nitriles as Novel Supramolecular Building Blocks: Four-Center Se···N Chalcogen Bonding versus Other Weak Interactions

Supramolecular chemistry of chalcogenadiazoles is attracting an increasing attention due to its applications in materials chemistry. Chalcogen bonding allows a fine-tuning of the self-assembly and, therefore, modulation of physical properties when these compounds are employed. Here, we report a facile preparation of a broad scope of 1,2,4-selenadiazoles via coupling of 2-pyridylselenenyl halides with unactivated nitriles, that represent a novel type of supramolecular building blocks which eagerly engage in a variety of chalcogen bonding interactions. The substituent-dependent propensity of novel selenadiazoles for the formation of four-center Se···N chalcogen bonding is analyzed. Other weak interactions, which in some cases outcompete the formation of 2Se-2N squares, are described. The discovery of the adducts derived from α-halogenated nitriles, which form robust dimers featuring a very specific combination of 2Se-2N square, two Hal···Hal, and two Se···Hal noncovalent interactions, is presented. © 2021 American Chemical Society.

American Chemical Society
  • 1 Peoples' Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
  • 2 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow, 119991, Russian Federation
  • 3 Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 31, Moscow, 119071, Russian Federation
  • 4 R.E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, Nizhny Novgorod, 603155, Russian Federation
  • 5 Institute of Chemistry, Vietnam Academy of Science and Technology, A18, Hanoi, Viet Nam
  • 6 N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Ul. Kosygina 4, Moscow, 119991, Russian Federation
  • 7 M.V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow, 119991, Russian Federation
Chemical bonds; Dimers; Ions; Selenium compounds; Supramolecular chemistry; Bonding interactions; Building blockes; Chalcogens; Facile preparation; Fine tuning; ITS applications; Material chemistry; Non-covalent interaction; Weak interactions; Cyanides
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