ArticleJournal of the American Chemical Society2019
Secondary Orbital Interactions Enhance the Reactivity of Alkynes in Diels-Alder Cycloadditions.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 13 papers.
What it found
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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.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
13 citing papers in PubMed, 35 citations in OpenAlex.
- Heat- and Light-Directed Cycloadditions Enable a Pericyclic Cascade Reaction From a Molecular Precursor.Angewandte Chemie (International ed. in English) · 2026Article
- Insights into Tetrazine-Benzene Cycloadditions.The journal of physical chemistry. A · 2026Article
- Hyperpyramidalized alkenes with bond orders near 1.5 as synthetic building blocks.Nature chemistry · 2026Article
- Advancing sulfide solid electrolytes via green LiNature communications · 2025Article
- Understanding Bio-Orthogonal Strain-Driven Sydnone Cycloadditions: Data-Assisted Profiles and the Search for Linear Relationships.Molecules (Basel, Switzerland) · 2025Article
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
- Click Organocatalysis: Acceleration of Azide-Alkyne Cycloadditions with Mutually Orthogonal Click Reactions.The Journal of organic chemistry · 2024Article
- Article
- Computational study of an oxetane 4Tetrahedron letters · 2023Article
- How Bases Catalyze Diels-Alder Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Oxidation-Induced "One-Pot" Click Chemistry.Chemical reviews · 2021Article
- Click Chemistry with Cyclopentadiene.Chemical reviews · 2021Review
- Aromatic hydrocarbon belts.Nature chemistry · 2021Review
Corrections and comments
- Erratum issued
Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
We have investigated the inverse electron-demand Diels-Alder reactions of trans-cyclooctene (TCO) and endo-bicyclo[6.1.0]nonyne (BCN) with a 1,2,4,5-tetrazine, a cyclopentadienone, and an ortho-benzoquinone. Tetrazines react significantly faster with TCO compared to BCN because the highest occupied molecular orbital (HOMO) of TCO is significantly higher in energy than the HOMO of BCN and there is less distortion of the tetrazine. Despite the different HOMO energies, TCO and BCN have similar reactivities toward cyclopentadienones, while BCN is significantly more reactive than TCO in the cycloaddition with ortho-benzoquinone. We find that the higher reactivity of BCN compared to TCO with ortho-benzoquinone is due to secondary orbital interactions of the BCN HOMO-1 with the diene LUMO.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.