1. Angle-strained sila-cycloalkynes.
- Author
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Wakefield IV, Herbert, Melvin, Sophia J., Jiang, Jennifer, Kevlishvili, Ilia, Siegler, Maxime A., Craig, Stephen L., Kulik, Heather J., and Klausen, Rebekka S.
- Subjects
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PERICYCLIC reactions , *CHEMICAL engineering , *GIBBS' energy diagram , *ACTIVATION energy , *CHEMICAL decomposition , *RING formation (Chemistry) - Abstract
This article in Chemical Communications explores the synthesis and reactivity of angle-strained sila-cycloalkynes. The authors present the synthesis of two new examples of these compounds and investigate their reactivity with azides. The results indicate that angle-strain alone is not enough to facilitate cycloaddition at room temperature, which has implications for the field of organic chemistry and chemical biology. The article includes detailed experimental procedures and computational details for further study. Additionally, the document discusses the lack of reaction between a specific sila-cyclooctyne compound and N3Bn at different temperatures. The authors suggest that the slow reaction rate may be due to modest alkyne distortion and the electron-donating effect of the silicon atom. Computational studies support this hypothesis, showing that the activation energies of the reaction increase across the series of compounds, consistent with the experimental rates. In conclusion, the article emphasizes that measurable angle strain alone cannot accurately predict strain-promoted azide-alkyne cycloaddition reactions at room temperature. [Extracted from the article]
- Published
- 2024
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