Lewis ambiphilicity of 1,2,5-chalcogenadiazoles for crystal engineering: Complexes with crown ethers

Lewis ambiphilicity of 1,2,5-chalcogenadiazoles for crystal engineering: Complexes with crown ethers Full article

Journal

Crystal Growth and Design
ISSN: 1528-7483 , E-ISSN: 1528-7505

Output data

Year: 2020, Volume: 20, Number: 9, Pages: 5868-5879 Pages count : 12 DOI: 10.1021/acs.cgd.0c00536

Authors

Chulanova E.A. ¹ , Radiush E.A. ¹ , Shundrina I.K. ¹ , Bagryanskaya I.Y. ¹ , Semenov N.A. ¹ , Beckmann J. ² , Gritsan N.P. ³ , Zibarev A.V. ¹

Affiliations

1	(Scopus) Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, 630090, Russian Federation
2	(Scopus) Institute for Inorganic Chemistry and Crystallography, University of Bremen, Bremen, 28359, Germany
3	(Scopus) Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, Novosibirsk, 630090, Russian Federation

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-18-c-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. Copyright © 2020 American Chemical Society.

Chulanova E.A. , Radiush E.A. , Shundrina I.K. , Bagryanskaya I.Y. , Semenov N.A. , Beckmann J. , Gritsan N.P. , Zibarev A.V.
Lewis ambiphilicity of 1,2,5-chalcogenadiazoles for crystal engineering: Complexes with crown ethers
Crystal Growth and Design. 2020. V.20. N9. P.5868-5879. DOI: 10.1021/acs.cgd.0c00536 WOS Scopus

Published online:	Jul 13, 2020
Published print:	Sep 2, 2020

Web of science	WOS:000569269800027
Scopus	2-s2.0-85092222996
OpenAlex	W3042520500