ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Understanding the 1,3-Dipolar Cycloadditions of Allenes.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 28 citations in OpenAlex.
- PyOrbb-Automated Analyses of Orbital-Interaction Mechanisms.Journal of computational chemistry · 2026Article
- Diradical Character of Cyclic Allenes Enables Their Thermal (2 + 2) Cycloadditions.Journal of the American Chemical Society · 2026Article
- Identifying Reactivity Differences of Two-Carbon-Atom-Based Legacy Refrigerants at Group 9 Metal Pincer Complexes.ACS organic & inorganic Au · 2025Article
- Density Functional Theory Calculations: A Useful Tool to Investigate Mechanisms of 1,3-Dipolar Cycloaddition Reactions.International journal of molecular sciences · 2024Review
- How Bases Catalyze Diels-Alder Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design.Chemistry, an Asian journal · 2022Review
- Pericyclic reaction benchmarks: hierarchical computations targeting CCSDT(Q)/CBS and analysis of DFT performance.Physical chemistry chemical physics : PCCP · 2022Article
- Quantification of the Helicality of Helical Molecular Orbitals.The journal of physical chemistry. A · 2021Article
- Zinc Iodide Catalyzed Synthesis of Trisubstituted Allenes from Terminal Alkynes and Ketones.ACS omega · 2021Article
- Switch From Pauli-Lowering to LUMO-Lowering Catalysis in Brønsted Acid-Catalyzed Aza-Diels-Alder Reactions.ChemistryOpen · 2021Article
- Origins of Endo Selectivity in Diels-Alder Reactions of Cyclic Allene Dienophiles.Angewandte Chemie (International ed. in English) · 2021Article
- Chemical reactivity from an activation strain perspective.Chemical communications (Cambridge, England) · 2021Review
- How Oriented External Electric Fields Modulate Reactivity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- How the Lewis Base FThe Journal of organic chemistry · 2021Article
- Understanding the 1,3-Dipolar Cycloadditions of Allenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
We have quantum chemically studied the reactivity, site-, and regioselectivity of the 1,3-dipolar cycloaddition between methyl azide and various allenes, including the archetypal allene propadiene, heteroallenes, and cyclic allenes, by using density functional theory (DFT). The 1,3-dipolar cycloaddition reactivity of linear (hetero)allenes decreases as the number of heteroatoms in the allene increases, and formation of the 1,5-adduct is, in all cases, favored over the 1,4-adduct. Both effects find their origin in the strength of the primary orbital interactions. The cycloaddition reactivity of cyclic allenes was also investigated, and the increased predistortion of allenes, that results upon cyclization, leads to systematically lower activation barriers not due to the expected variations in the strain energy, but instead from the differences in the interaction energy. The geometric predistortion of cyclic allenes enhances the reactivity compared to linear allenes through a unique mechanism that involves a smaller HOMO-LUMO gap, which manifests as more stabilizing orbital interactions.
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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.