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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.3K
Prochirality02:05

Prochirality

4.8K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
4.8K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.6K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.6K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.1K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

20.8K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
20.8K

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Topological classification of cycloadditions occurring on-surface and in the solid-state.

Juan Li1,2, Amir Mirzanejad3, Wen-Han Dong4

  • 1School of Interdisciplinary Science, Beijing Institute of Technology, 100081, Beijing, China.

Communications Chemistry
|December 3, 2025
PubMed
Summary

Topological tools classify symmetry-forbidden cycloaddition reactions. This advances nanographene engineering by revealing allowed pathways for endothermic reactions, crucial for designing new materials.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Cycloaddition mechanisms are key to synthesizing sp2 carbon nanostructures like graphene.
  • Current reaction modeling often overlooks symmetry effects, focusing only on exothermic products.

Purpose of the Study:

  • To introduce a method for classifying symmetry-forbidden reaction pathways using topological tools.
  • To explore the role of topological classification in understanding cycloaddition mechanisms for nanographene engineering.

Main Methods:

  • Development of a scheme for classifying symmetry-forbidden reaction coordinates in Woodward-Hoffmann diagrams.
  • Application of topological classifiers to analyze polycyclic aromatic azomethine ylide (PAMY) cycloadditions.
  • Utilizing tight-binding reaction models and broken-symmetry density functional theory (DFT).

Main Results:

  • Topological classifiers provide a unified approach to studying reaction pathways and correlation diagrams.
  • Identified topologically-allowed pathways for an endothermic reaction mechanism in PAMY cycloadditions.
  • Demonstrated that exothermic pathways can be topologically forbidden.

Conclusions:

  • Topological classification is essential for accurate reaction modeling in nanographene engineering.
  • This approach is fundamental for designing on-surface and solid-state cycloaddition reactions.
  • Highlights the importance of considering symmetry and topology beyond simple energetics.