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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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

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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.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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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.
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Predicting Reaction Outcomes02:24

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Kinetics describes the rate and path by which a reaction occurs. In contrast, thermodynamics deals with state functions and describes the properties, behavior, and components of a system. It is not concerned with the path taken by the process and cannot address the rate at which a reaction occurs. Although it does provide information about what can happen during a reaction process, it does not describe the detailed steps of what appears on an atomic or a molecular level. On the other hand,...
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SN1 Reaction: Kinetics02:05

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In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...
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SN2 Reaction: Kinetics02:14

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Kinetic Studies and Significance
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
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Predictive Models for Kinetic Parameters of Cycloaddition Reactions.

Marta Glavatskikh1,2, Timur Madzhidov2, Dragos Horvath1

  • 1Laboratoire de Chémoinformatique, UMR 7140 CNRS, Université de Strasbourg, 1, rue Blaise Pascal, 67000, Strasbourg, France.

Molecular Informatics
|August 23, 2018
PubMed
Summary

This study models cycloaddition reaction kinetics using Support Vector Regression and Generative Topographic Mapping. The models accurately predict reaction rate constants, activation energies, and pre-exponential factors for diverse chemical transformations.

Keywords:
Condensed Graph of ReactionGenerative Topographic MappingQSPRcycloaddition reactions

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Area of Science:

  • Computational Chemistry
  • Chemical Kinetics
  • Machine Learning in Chemistry

Background:

  • Cycloaddition reactions are fundamental in organic synthesis.
  • Predicting reaction kinetics (rate constant, activation energy, pre-exponential factor) is crucial for reaction design.
  • Existing methods for kinetic property prediction often lack broad applicability across different reaction types and conditions.

Purpose of the Study:

  • To develop predictive models for key kinetic properties of cycloaddition reactions.
  • To explore the utility of Support Vector Regression (SVR) and Generative Topographic Mapping (GTM) for kinetic property prediction.
  • To encode reactions using ISIDA fragment descriptors within a Condensed Graph of Reaction (CGR) framework.

Main Methods:

  • Utilized a dataset of 1849 cycloaddition reactions ((4+2), (3+2), (2+2) CA).
  • Employed ISIDA fragment descriptors and Condensed Graph of Reaction (CGR) for reaction encoding.
  • Applied Support Vector Regression (SVR) and Generative Topographic Mapping (GTM) for modeling logk, Ea, and logA.
  • Investigated direct modeling, Arrhenius equation, and temperature-scaled GTM landscapes for logk assessment.

Main Results:

  • Achieved high cross-validated statistics for logk models (Q² =0.78-0.94, RMSE=0.45-0.86).
  • Successfully predicted reaction rates for an external test set of 200 reactions under varied conditions.
  • Demonstrated the effectiveness of CGR-encoded ISIDA descriptors in SVR and GTM models.

Conclusions:

  • SVR and GTM models provide accurate predictions of cycloaddition reaction kinetics.
  • The CGR framework effectively represents complex chemical transformations for machine learning.
  • Developed predictive models are accessible via a web server for broader scientific use.