Design, synthesis and isolation of a new 1,2,5-selenadiazolidyl and structural and magnetic characterization of its alkali-metal salts

Semenov, Nikolay A.; Radiush, Ekaterina A.; Chulanova, Elena A.; Slawin, Alexandra M. Z.; Woollins, J. Derek; Kadilenko, Evgeny M.; Bagryanskaya, I. Yu.; Irtegova, Irina G.; Bogomyakov, A. S.; Shundrin, Leonid A.; Gritsan, Nina P.; Zibarev, Andrey V.

doi:10.1039/c9nj04069b

Cited by 13 publications

(13 citation statements)

References 38 publications

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“…Compound 1 was synthesized according to the slightly modified literature procedure. 13 18-crown-6, […”

Section: Generalmentioning

confidence: 99%

“…1 They are best known as p-acceptors for conductive materials for organic electronics, 2,3 and charge-transfer (CT) complexes, 4 as well as precursors of stable radical anions (RAs). [5][6][7][8][9][10][11][12][13] Their p-electronic structure can be finely tuned to such an extent that they act as electron acceptor and donor towards each other. 14 Also, chalcogenadiazoles exhibit s-donor properties, e.g.…”

Section: Introductionmentioning

confidence: 99%

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Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

et al. 2022

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“…Compound 1 was synthesized according to the slightly modified literature procedure. 13 18-crown-6, […”

Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

et al. 2022

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“…1,2,5-Chalcogenadiazoles and especially their fused derivatives (chalcogen E = S, Se, Te; Scheme ) are important for chemistry, materials science, and biomedicine. − Notably, they feature Lewis ambiphilicity, i.e., the ability to be Lewis acids and bases simultaneously, − which is dualistic since in both acidic and basic behavior both σ- and π-molecular orbitals (MO) are involved. Examples include the self-association of 1,2,5-chalcogenadiazoles by means of [E···N] 2 supramolecular synthons in crystal lattices of neutral ,− and charged derivatives covering 1,2,5-chalcogenadiazolidyl and 1-methyl 1,2,5-chalcogenadiazolylium salts; the formation of radical anions (RAs) ,,− and charge transfer (CT) complexes (where they can function as both A and D); ,− and metal coordination compounds ,− (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Lewis Ambiphilicity of 1,2,5-Chalcogenadiazoles for Crystal Engineering: Complexes with Crown Ethers

Chulanova

Radiush

Shundrina

et al. 2020

Crystal Growth & Design

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The cocrystallization of 1,2,5-chalcogenadiazoles (chalcogen E = S, Se, and Te) with cyclic polyethers 18-crown-6 (18-c-6) and dibenzo-18-crown-6 (db-18c-6) yielded the molecular complexes characterized by X-ray diffraction and thermogravimetry/differential scanning calorimetry techniques together with density functional theory (DFT) calculations and quantum theory of atoms in molecule and natural bond orbitals analysis. The complexes are bound by multiple secondary bonding interactions, the most important of which reflects the Lewis ambiphilicity of 1,2,5-chalcogenadiazoles and includes charge transfer from O atoms of the ethers onto E atoms of the chalcogenadiazoles (i.e., chalcogen bonding), and the back-donation from E to O. For complexes of 18-c-6, the DFT-calculated energies of bonding interactions correlate with the melting temperatures of the complexes, as well as with the atomic number of E and the size of the E-associated σ-holes but not with the maximum of molecular electrostatic potential at the σ-holes. Taking into account the previous results, the Lewis ambiphilicity of 1,2,5-chalcogenadiazoles may be used for applications in crystal engineering.

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“…There are seven two-dimensional arrays featuring Se … N interactions between the molecules: 116 [145], 117 [146], 118 [147], 119 [128], 120 [148], 121 [149] and 122 [150].…”

Section: Two-and Three-dimensional Architectures Featuring Se … N Interactionsmentioning

confidence: 99%

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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An evaluation of the Cambridge Structural Database for crystals containing Se … N secondary--bonding interactions was conducted. The presence of Se … N secondary-bonding interactions has been established in nearly 9% of crystals of mono-nuclear selenium compounds where such interactions can potentially form, that is, having at least one nitrogen atom. The Se … N interactions feature in 71 zero-dimensional, usually di-nuclear aggregates, 63 one-dimensional chains and tapes, and smaller numbers of two-and three-dimensional arrays, that is seven and one, respectively. Selenium(II) compounds form the majority of the dataset with only eight selenium(IV) compounds included in the survey. In most cases (112 out of 142), the selenium centre forms a single Se … N contact with 26 aggregates having a selenium atom forming two contacts and four examples where three Se … N contacts are evident. The great propensity of selenadiazole rings (75%) and selenocyanates (50%) to form Se … N secondary-bonding interactions in their crystals is particularly noteworthy.

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Design, synthesis and isolation of a new 1,2,5-selenadiazolidyl and structural and magnetic characterization of its alkali-metal salts

Abstract: A new electron acceptor is synthesized and reduced into its radical-anion isolated in the form of two salts with different structures and magnetic properties.

Cited by 13 publications

References 38 publications

Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions

Lewis Ambiphilicity of 1,2,5-Chalcogenadiazoles for Crystal Engineering: Complexes with Crown Ethers

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

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