ArticleThe Journal of organic chemistry2022
In the Chalcogenoxide Elimination Panorama: Systematic Insight into a Key Reaction.
Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- A Crystalline and Thermally Stable Selenocysteine Selenenic Acid.Angewandte Chemie (International ed. in English) · 2026Article
- Dihalogens Binding and Activation by Imidazoline-2-Chalcogenone Model Derivatives: Insight from a Computational Approach.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- A Computational Study of Heteroatom Analogues of Selenoxide and SelenoneMolecules (Basel, Switzerland) · 2024Article
- Untangling the catalytic importance of the Se oxidation state in organoselenium-mediated oxygen-transfer reactions: the conversion of aniline to nitrobenzene.Chemical science · 2024Article
- The Key Role of Chalcogenurane Intermediates in the Reduction Mechanism of Sulfoxides and Selenoxides by Thiols Explored In Silico.International journal of molecular sciences · 2023Article
Corrections and comments
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Authors and funding
5 authors.
Funding
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Abstract
The selenoxide elimination is a well-known reaction in organochalcogen chemistry, with wide synthetic, biological, and toxicological implications. In this work, we apply benchmarked density functional theory (DFT) calculations to investigate different aspects of the title reaction in three (bio)chemically relevant models, spanning minimal systems of theoretical interests as well as biological or synthetic organochalcogenides. The activation strain analysis (ASA) methodology is employed along a suitable reaction coordinate to obtain insight into the role of the chalcogen and of the oxidation state, to pinpoint the factors that tune the elimination reactivity of the investigated systems. Lastly, we computationally validate the hypothesis that telluroxides eliminate more slowly than selenoxides because of a detrimental hydration process that leads to unreactive hydrates.
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Registered trials
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