Stable Carbenes as Structural Components of Partially Saturated Sulfur-Containing Heterocycles

Autor:	Alexander B. Rozhenko, Yuliia S. Horbenko, Andrii A. Kyrylchuk, Evgenij V. Zarudnitskii, Sergiy S. Mykhaylychenko, Yuriy G. Shermolovich, Andriy V. Grafov
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	stable carbenes ab initio calculations thiadiazolines bond elongation Organic chemistry QD241-441
Zdroj:	Molecules, Vol 27, Iss 5, p 1458 (2022)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules27051458
Popis:	Recently, an unusual elongation of the C-S bond was observed experimentally for some sulfur-containing heterocycles. Using a superior ab initio (SCS-MP2/cc-pVTZ) level of theory, we showed that the phenomenon can be explained by a contribution of a donor–acceptor adduct of a carbene with an unsaturated ligand. One may achieve further elongation of the C-S bond, eventually turning it to a coordinate one, by increasing the stability of each part of the system as, e.g., in the utmost case of spiro adducts with Arduengo carbenes. The effect of carbene stability was quantified by employing the isodesmic reactions of carbene exchange.
Databáze:	Directory of Open Access Journals
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