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Acta Cryst. (2014). A70, C1796
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Recently we reported a new possibility for stabilizing highly reactive organoselenenyl(II) chlorides by N-functionalization of an organyl substituent and the subsequent addition of a hydrochloric acid molecule [Ref.]. It is well-known that organotellurenyl(II) chlorides are even less stable than the related organoselenenyl(II) chlorides. This fact prompted us to apply the same approach to organotellurenyl(II) chlorides containing an N-functionalized aryl substituent. In the present work, a novel facile route for stabilizing highly reactive Ar*TeCl species (Ar* = nitrogen-containing aryl) by hydrochloric acid addition has been demonstrated, exemplified by two new T-shaped tellurenyl chloride adducts, viz. 1H-pyridine-2-tellurenyl-dichloride (Fig.) and 4,6-dimethyl-1H-pyrimidine-2-tellurenyl-dichloride. Their quasi-planar zwitterionic structures with strong intramolecular N-H...Cl hydrogen bonds have been evidenced by experimental (single-crystal X-ray diffraction, multi-nuclear NMR, vibrational spectroscopy) and theoretical (DFT and QTAIM) methods. Due to this structure, the studied heteroaryl tellurenyl dichlorides react with alkenes in a similar manner to the corresponding monomeric tellurenyl chlorides affording the same cycloaddition products. The described approach to difficult-to-obtain, extremely unstable organotellurenyl(II) chlorides opens alluring prospects in the synthesis and study of low-valent chalcogen compounds.

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