ArticleThe Journal of organic chemistry2021
Computational Exploration of Ambiphilic Reactivity of Azides and Sustmann's Paradigmatic Parabola.
Article in The Journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 17 citations in OpenAlex.
- Recyclable Hydrotalcite-Supported Copper Catalysts for Green and Regioselective Click Synthesis of 1,2,3-Triazoles.ACS omega · 2026Article
- Comparative computational analysis of orthoconic antiferroelectric liquid crystals: DFT analysis.Journal of molecular modeling · 2024Article
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
- Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism.The Journal of organic chemistry · 2024Article
- Click Organocatalysis: Acceleration of Azide-Alkyne Cycloadditions with Mutually Orthogonal Click Reactions.The Journal of organic chemistry · 2024Article
- Mechanistic DFT Study of 1,3-Dipolar Cycloadditions of Azides with Guanidine.Molecules (Basel, Switzerland) · 2023Article
- The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design.Chemistry, an Asian journal · 2022Review
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
We examine the theoretical underpinnings of the seminal discoveries by Reiner Sustmann about the ambiphilic nature of Huisgen's phenyl azide cycloadditions. Density functional calculations with ωB97X-D and B2PLYP-D3 reproduce the experimental data and provide insights into ambiphilic control of reactivity. Distortion/interaction-activation strain and energy decomposition analyses show why Sustmann's use of dipolarophile ionization potential is such a powerful predictor of reactivity. We add to Sustmann's data set several modern distortion-accelerated dipolarophiles used in bioorthogonal chemistry to show how these fit into the orbital energy criteria that are often used to understand cycloaddition reactivity. We show why such a simple indicator of reactivity is a powerful predictor of reaction rates that are actually controlled by a combination of distortion energies, charge transfer, closed-shell repulsion, polarization, and electrostatic effects.
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Registered trials
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