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Sapronov, Alexander A; Artemjev, Alexey A; Burkin, Gleb M; Khrustalev, Victor N; Kubasov, Alexey S; Nenajdenko, Valentine G; Gomila, Rosa M; Frontera, Antonio; Kritchenkov, Andreii S; Tskhovrebov, Alexander G
International journal of molecular sciences, 11/2022, Letnik: 23, Številka: 23Journal Article
The series of benzylic-substituted 1,2,4-selenodiazolium salts were prepared via cyclization reaction between 2-pyridylselenyl chlorides and nitriles and fully characterized. Substitution of the Cl anion by weakly binding anions promoted the formation supramolecular dimers featuring four center Se N chalcogen bonding and two antiparallel selenium⋯π interactions. Chalcogen bonding interactions were studied using density functional theory calculations, molecular electrostatic potential (MEP) surfaces, the quantum theory of atoms-in-molecules (QTAIM), and the noncovalent interaction (NCI) plot. The investigations revealed fundamental role of the selenium⋯π contacts that are stronger than the Se⋯N interactions in supramolecular dimers. Importantly, described herein, the benzylic substitution approach can be utilized for reliable supramolecular dimerization of selenodiazolium cations in the solid state, which can be employed in supramolecular engineering.
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