ArticleChemistry (Weinheim an der Bergstrasse, Germany)2023
Substituent Effects in Bioorthogonal Diels-Alder Reactions of 1,2,4,5-Tetrazines.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Insights into Tetrazine-Benzene Cycloadditions.The journal of physical chemistry. A · 2026Article
- strainedSMILES2xyz: a workflow for reliable 3D structures of strained molecules from SMILES.Journal of cheminformatics · 2026Article
- Investigation of Proteome-Tetrazine Reactivity for a Highly Selective Tetrazine Ligation in Live Cells.ACS central science · 2025Article
- Computational Investigation of a COACS omega · 2025Article
- Ortho-functionalized pyridinyl-tetrazines break the inverse correlation between click reactivity and cleavage yields in click-to-release chemistry.Communications chemistry · 2024Article
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
- How cycloalkane fusion enhances the cycloaddition reactivity of dibenzocyclooctynes.Chemical science · 2024Article
- Article
- Unraveling the Bürgi-Dunitz Angle with Precision: The Power of a Two-Dimensional Energy Decomposition Analysis.Journal of chemical theory and computation · 2023Article
- Substituent Effects in Bioorthogonal Diels-Alder Reactions of 1,2,4,5-Tetrazines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
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Authors and funding
3 authors.
Funding
Abstract
1,2,4,5-Tetrazines are increasingly used as reactants in bioorthogonal chemistry due to their high reactivity in Diels-Alder reactions with various dienophiles. Substituents in the 3- and 6-positions of the tetrazine scaffold are known to have a significant impact on the rate of cycloadditions; this is commonly explained on the basis of frontier molecular orbital theory. In contrast, we show that reactivity differences between commonly used classes of tetrazines are not controlled by frontier molecular orbital interactions. In particular, we demonstrate that mono-substituted tetrazines show high reactivity due to decreased Pauli repulsion, which leads to a more asynchronous approach associated with reduced distortion energy. This follows the recent Vermeeren-Hamlin-Bickelhaupt model of reactivity increase in asymmetric Diels-Alder reactions. In addition, we reveal that ethylene is not a good model compound for other alkenes in Diels-Alder reactions.
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