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MDPI, Symmetry, 12(13), p. 2350, 2021

DOI: 10.3390/sym13122350

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2-Pyridylselenenyl versus 2-Pyridyltellurenyl Halides: Symmetrical Chalcogen Bonding in the Solid State and Reactivity towards Nitriles

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The synthesis of 2-pyridyltellurenyl bromide via Br2 oxidative cleavage of the Te–Te bond of dipyridylditelluride is reported. Single-crystal X-ray diffraction analysis of 2-pyridyltellurenyl bromide demonstrated that the Te atom of 2-pyridyltellurenyl bromide was involved in four different noncovalent contacts: Te⋯Te interactions, two Te⋯Br ChB, and one Te⋯N ChB contact forming 3D supramolecular symmetrical framework. In contrast to 2-pyridylselenenyl halides, the Te congener does not react with nitriles furnishing cyclization products. 2-Pyridylselenenyl chloride was demonstrated to easily form the corresponding adduct with benzonitrile. The cyclization product was studied by the single-crystal X-ray diffraction analysis, which revealed that in contrast to earlier studied cationic 1,2,4-selenadiazoles, here we observed that the adduct with benzonitrile formed supramolecular dimers via Se⋯Se interactions in the solid state, which were never observed before for 1,2,4-selenadiazoles.