Investigation in the field of aromatic heterocycles

Todres, Z. V.; Zhdanov, S. I.; Tsveniashvili, V. Sh.

doi:10.1007/bf00910820

Cited by 2 publications

(1 citation statement)

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“…For applications, anion recognition and sensing in water are especially important. To this end, water‐stable 2,1,3‐benzoselenadiazoles [139] can be tailored by means of carbocyclic substitution with hydrophilic groups, e. g. −[SO 3 ] − , [140,141] or/and by annulation with hydrophilic scaffolds. In the context of crystal engineering, this work demonstrates how minor variations of the molecular structure allow to tune the propensity of chalcogenadiazole derivatives towards cocrystallization with Lewis bases, while the magnitude of V S,max of the σ‐hole at a chalcogen remains almost the same, unlike in previous reports, where the main reason of the cocrystallization is a certain magnitude of V S,Max at the σ‐hole at a chalcogen.…”

Section: Discussionmentioning

confidence: 99%

Halide Complexes of 5,6‐Dicyano‐2,1,3‐Benzoselenadiazole with 1 : 4 Stoichiometry: Cooperativity between Chalcogen and Hydrogen Bonding

Radiush,

Wang,

Chulanova

et al. 2023

ChemPlusChem

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The [M4–Hal]– (M = the title compound; Hal = Cl, Br, and I) complexes were isolated in the form of salts of [Et4N]+ cation and characterized by XRD, NMR, UV‐Vis, DFT, QTAIM, EDD, and EDA. Their stoichiometry is caused by a cooperative interplay of σ‐hole‐driven chalcogen (ChB) and hydrogen (HB) bondings. In the crystal, [M4–Hal]– are connected by the π‐hole‐driven ChB; overall, each [Hal]– is six‐coordinated. In the ChB, the electrostatic interaction dominates over orbital and dispersion interactions. In UV‐Vis spectra of the M + [Hal]– solutions, ChB‐typical and [Hal]–‐dependent charge‐transfer bands are present; they reflect orbital interactions and allow identification of the individual [Hal]–. However, the structural situation in the solutions is not entirely clear. Particularly, the UV‐Vis spectra of the solutions are different from the solid‐state spectra of the [Et4N]+[M4–Hal]–; very tentatively, species in the solutions are assigned [M–Hal]–. It is supposed that the formation of the [M4–Hal]– proceeds during the crystallization of the [Et4N]+[M4–Hal]–. Overall, M can be considered as a chromogenic receptor and prototype sensor of [Hal]–. The findings are also useful for crystal engineering and supramolecular chemistry.

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Section: Discussionmentioning

confidence: 99%