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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
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.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
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.
3.6K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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.
2.2K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.4K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
8.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.4K
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.
10.4K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Reaction profiles for quantum chemistry-computed [3 + 2] cycloaddition reactions.

Thijs Stuyver1, Kjell Jorner2,3,4, Connor W Coley5,6

  • 1Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts, 02139, USA.

Scientific Data
|February 1, 2023
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Summary

Researchers developed an automated workflow to compute over 5000 reaction profiles for bio-orthogonal click chemistry. This computational approach aids in screening new reactions and developing predictive models for chemical reactivity.

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Area of Science:

  • Biochemistry
  • Computational Chemistry
  • Chemical Biology

Background:

  • Bio-orthogonal click chemistry, particularly [3+2] dipolar cycloadditions, is crucial in biochemistry.
  • Identifying new reactions requires understanding on- and off-target activation and reaction energies.

Purpose of the Study:

  • To develop and apply an automated workflow for computing reaction profiles of [3+2] cycloadditions.
  • To assess the suitability of potential reactions for bio-orthogonal applications.

Main Methods:

  • Utilized the autodE program for automated reaction profile computation.
  • Calculated over 5000 reaction profiles for [3+2] cycloadditions with synthetic dipolarophiles and biologically-inspired motifs.
  • Employed DFT calculations at the B3LYP-D3(BJ)/def2-TZVP//B3LYP-D3(BJ)/def2-SVP level of theory under physiological conditions (aqueous SMD model).

Main Results:

  • Generated a large dataset of reaction profiles for diverse [3+2] cycloadditions.
  • Established a robust computational workflow for high-throughput screening of chemical reactions.
  • Provided valuable data for identifying novel bio-orthogonal reactions.

Conclusions:

  • The developed automated workflow and computed data are valuable resources for discovering new bio-orthogonal click reactions.
  • This approach can facilitate the development of machine learning models for predicting chemical reactivity.
  • Enables efficient screening of reactions for biochemical applications.