Palladium(II)-Stabilized Pyridine-2-Diazotates: Synthesis, Structural Characterization, and Cytotoxicity Studies

Tskhovrebov, Alexander G.; Vasil'eva, A. A.; Goddard, Richard; Riedel, Tina; Dyson, Paul J.; Mikhaylov, Vladimir N.; Serebryanskaya, Tatiyana V.; Sorokoumov, V. N.; Haukka, Matti

doi:10.1021/acs.inorgchem.8b00072

Cited by 29 publications

(15 citation statements)

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“…The N–Se distance for 3 – 10 was in the interval between 1.824(3) Å and 1.860(4) Å, and was typical for the N–Se single bond. The C=N separation (1.25(1)–1.291(5) Å for 3 – 10 ) corresponded to a typical double bond [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ].…”

Section: Resultsmentioning

confidence: 99%

Exploring Supramolecular Assembly Space of Cationic 1,2,4-Selenodiazoles: Effect of the Substituent at the Carbon Atom and Anions

et al. 2022

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Chalcogenodiazoles have been intensively studied in recent years in the context of their supramolecular chemistry. In contrast, the newly discovered cationic 1,2,4-selenodiazole supramolecular building blocks, which can be obtained via coupling between 2-pyridylselenyl halides and nitriles, are virtually unexplored. A significant advantage of the latter is their facile structural tunability via the variation of nitriles, which could allow a fine tuning of their self-assembly in the solid state. Here, we explore the influence of the substituent (which derives from the nitrile) and counterions on the supramolecular assembly of cationic 1,2,4-selenodiazoles via chalcogen bonding.

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Section: Resultsmentioning

confidence: 99%

Exploring Supramolecular Assembly Space of Cationic 1,2,4-Selenodiazoles: Effect of the Substituent at the Carbon Atom and Anions

et al. 2022

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“…Recently we demonstrated that 2-pyridylselenenyl halides selectively react with a broad scope of nitriles to form adducts 3-14 in excellent yields (Scheme 1) [11,29]. Within this work, following our interest in CN and NN triple bond activation [30][31][32][33][34][35][36][37][38][39][40][41][42][43], we attempted to prepare analogous Te derivatives. 2-Pyridyltellurenyl bromide (16 was easily synthesized by the oxidation of di-(2-pyridyl)-ditelluride with molecula bromine.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2021

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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.

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“…The amine N atom is significantly flattened due to conjugation with a vinyl group, the C1-S1-N1-C13 torsion angle being 28.46 (13) . The N1-C13 bond distance [1.4138 (13) Å ] is slightly shorter than that of a standard C-N single bond in similar compounds (Tskhovrebov et al, 2012(Tskhovrebov et al, , 2014(Tskhovrebov et al, , 2018Repina et al, 2020). The molecular structure features an intramolecular S1 O4Á Á ÁH12B-C12 hydrogen bond (Table 1), leading to the formation of an S(13) macrocycle in the crystal.…”

Section: Structural Commentarymentioning

confidence: 98%

Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide

Temesgen¹,

Luong²,

Truong³

et al. 2020

Acta Cryst E

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The title compound, C21H23NO4S, obtained by alkaline treatment of 1,5-bis(1-phenoxy)-3-azapentane at moderate heating, is a N-tosylated secondary vinylamine. An intramolecular S=O...H—C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with respect to the C=C double bond, which is slightly longer than usual due to the conjugation with a neighbouring acetyl group. Theoretical predictions of potential biological activities were performed, suggesting that the title compound can inhibit gluconate 2-dehydrogenase (85% probability), as well as to act as a mucomembranous protector (73%).

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Palladium(II)-Stabilized Pyridine-2-Diazotates: Synthesis, Structural Characterization, and Cytotoxicity Studies

Cited by 29 publications

References 50 publications

Exploring Supramolecular Assembly Space of Cationic 1,2,4-Selenodiazoles: Effect of the Substituent at the Carbon Atom and Anions

Exploring Supramolecular Assembly Space of Cationic 1,2,4-Selenodiazoles: Effect of the Substituent at the Carbon Atom and Anions

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

Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide

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