ArticleChemistry (Weinheim an der Bergstrasse, Germany)2019
Dual Activation of Aromatic Diels-Alder Reactions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- The concept of aromaticity after 200 years of benzene.Nature reviews. Chemistry · 2026Review
- The application of aromaticity and antiaromaticity to reaction mechanisms.Fundamental research · 2023Review
- Factors Controlling the Aluminum(I)-meta-Selective C-H Activation in Arenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Double hybrid DFT calculations with Slater type orbitals.Journal of computational chemistry · 2020Article
- How Alkali Cations Catalyze Aromatic Diels-Alder Reactions.Chemistry, an Asian journal · 2020Article
- Understanding the reactivity of polycyclic aromatic hydrocarbons and related compounds.Chemical science · 2020Review
- Distortion-Controlled Redshift of Organic Dye Molecules.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Dual Activation of Aromatic Diels-Alder Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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Abstract
The unusually fast Diels-Alder reactions of [5]cyclophanes were analyzed by DFT at the BLYP-D3(BJ)/TZ2P level of theory. The computations were guided by an integrated activation-strain and Kohn-Sham molecular orbital analysis. It is revealed why both [5]metacyclophane and [5]paracyclophane exhibit a significant rate enhancement compared to their planar benzene analogue. The activation strain analyses revealed that the enhanced reactivity originates from 1) predistortion of the aromatic core resulting in a reduced activation strain of the aromatic diene, and/or 2) enhanced interaction with the dienophile through a distortion-controlled lowering of the HOMO-LUMO gap within the diene. Both of these physical mechanisms and thus the rate of Diels-Alder cycloaddition can be tuned through different modes of geometrical distortion (meta versus para bridging) and by heteroatom substitution in the aromatic ring. Judicious choice of the bridge and heteroatom in the aromatic core enables effective tuning of the aromatic Diels-Alder reactivity to achieve activation barriers as low as 2 kcal mol
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