Adducts of 2-Pyridylselenenyl Halides and Nitriles as Novel Supramolecular Building Blocks: Four-Center Se···N Chalcogen Bonding versus Other Weak Interactions
Mariya V. Grudova, Victor N. Khrustalev, Alexey S. Kubasov, П. В. Страшнов, Zhanna V. Matsulevich, Julia M. Lukiyanova, Г. Н. Борисова, Andreii S. Kritchenkov, Maria M. Grishina, Alexey A. Artemjev, Ivan Buslov, В. К. Османов, Valentine G. Nenajdenko, Nguyen Q. Trung, А. В. Борисов, Alexander G. Tskhovrebov
Abstract
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.