ArticleThe Journal of organic chemistry2016
Decreasing Distortion Energies without Strain: Diazo-Selective 1,3-Dipolar Cycloadditions.
Article in The Journal of organic chemistry, 2016. 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.
- Article
- Accessing trifluoromethylated SuFEx-able pyrazoleRSC advances · 2025Article
- The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design.Chemistry, an Asian journal · 2022Review
- Uncovering the Key Role of Distortion in Bioorthogonal Tetrazine Tools That Defy the Reactivity/Stability Trade-Off.Journal of the American Chemical Society · 2022Article
- SuFExableThe Journal of organic chemistry · 2022Article
- Acceleration of 1,3-Dipolar Cycloadditions by Integration of Strain and Electronic Tuning.Journal of the American Chemical Society · 2021Article
- The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition.Angewandte Chemie (International ed. in English) · 2020Review
- Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs.Journal of the American Chemical Society · 2017Article
- Diazo Compounds: Versatile Tools for Chemical Biology.ACS chemical biology · 2016Review
- 1,3-Dipolar Cycloaddition with Diazo Groups: Noncovalent Interactions Overwhelm Strain.Organic letters · 2016Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The diazo group has attributes that complement those of the azido group for applications in chemical biology. Here, we use computational analyses to provide insights into the chemoselectivity of the diazo group in 1,3-dipolar cycloadditions. Dipole distortion energies are responsible for ∼80% of the overall energetic barrier for these reactions. Here, we show that diazo compounds, unlike azides, provide an opportunity to decrease that barrier substantially without introducing strain into the dipolarophile. The ensuing rate enhancement is due to the greater nucleophilic character of a diazo group compared to that of an azido group, which can accommodate decreased distortion energies without predistortion. The tuning of distortion energies with substituents in a diazo compound or dipolarophile can enhance reactivity and selectivity in a predictable manner. Notably, these advantages of diazo groups are amplified in water. Our findings provide a theoretical framework that can guide the design and application of both diazo compounds and azides in "orthogonal" contexts, especially for biological investigations.
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