Donor-Acceptor Complexes between 1,2,5-Chalcogenadiazoles (Te, Se, S) and the Pseudohalides CN - and XCN - (X=O, S, Se, Te).

Autor: Semenov NA; Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia., Gorbunov DE; Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia.; Department of Physics, Novosibirsk State University, 630090, Novosibirsk, Russia., Shakhova MV; Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia.; Department of Physics, Novosibirsk State University, 630090, Novosibirsk, Russia., Salnikov GE; Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia.; Department of Natural Sciences, Novosibirsk State University, 630090, Novosibirsk, Russia., Bagryanskaya IY; Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia., Korolev VV; Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia., Beckmann J; Institute for Inorganic Chemistry and Crystallography, University of Bremen, 28359, Bremen, Germany., Gritsan NP; Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia.; Department of Physics, Novosibirsk State University, 630090, Novosibirsk, Russia., Zibarev AV; Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia.; Department of Physics, Novosibirsk State University, 630090, Novosibirsk, Russia.; Department of Chemistry, Tomsk State University, 643050, Tomsk, Russia.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 Sep 03; Vol. 24 (49), pp. 12983-12991. Date of Electronic Publication: 2018 Jul 27.
DOI: 10.1002/chem.201802257
Abstrakt: Donor-acceptor (D-A) complexes between 3,4-dicyano-1,2,5-chalcogenadiazoles [chalcogen=Te (1 a), Se (1 b), S (1 c)] and the pseudohalides CN - and XCN - (X=O, S, Se, Te) were studied experimentally and theoretically. For 1 a, they were isolated as [K(18-crown-6)][1 a-CN] (2), [K(18-crown-6)][1 a-NCO] (3), [K(18-crown-6)][1 a-SCN] (4), [K(18-crown-6)][1 a-SeCN] (5), and [K][1 a-NCSe] (6) and characterized by X-ray diffraction (XRD), UV/Vis and NMR spectroscopy, and DFT and QTAIM calculations. For 1 b and 1 c, the complexes were not isolated due to unfavorable thermodynamics. In all isolated complexes, the D-A bonds, stabilized by negative hyperconjugation, were longer than the sum of the covalent radii and shorter than the sum of the van der Waals radii of the bonded atoms. In mixtures of 1 a, F - , and SeCN - , the complex [1 a-F] - was selectively formed in accordance with thermodynamics. The reaction of 1 a with SeCN - and the cyclic trimeric perfluoro-ortho-phenylene mercury afforded the complex [K(18-crown-6)][SCN]⋅(o-C 6 F 4 Hg) 3 , which was characterized by XRD.
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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