ArticleAngewandte Chemie (International ed. in English)2021
Solvation Effects on the Structure and Stability of Alkali Metal Carbenoids.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
2 citing papers in PubMed, 5 citations in OpenAlex.
- Isolation and Reactivity of Stannylenoids Stabilized by Amido/Imino Ligands.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Solvation Effects on the Structure and Stability of Alkali Metal Carbenoids.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
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Abstract
s-Block metal carbenoids are carbene synthons and applied in a myriad of organic transformations. They exhibit a strong structure-activity relationship, but this is only poorly understood due to the challenging high reactivity and sensitivity of these reagents. Here, we report on systematic VT and DOSY NMR studies, XRD analyses as well as DFT calculations on a sulfoximinoyl-substituted model system to explain the pronounced solvent dependency of the carbenoid stability. While the sodium and potassium chloride carbenoids showed high stabilities independent of the solvent, the lithium carbenoid was stable at room temperature in THF but decomposed at -10 °C in toluene. These divergent stabilities could be explained by the different structures formed in solution. In contrast to simple organolithium reagents, the monomeric THF-solvate was found to be more stable than the dimer in toluene, since the latter more readily forms direct Li/Cl interactions which facilitate decomposition via α-elimination.
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