Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)01:27

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination reactions can be...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

One-Pot Amidation/C─H Halogenation by an Efficient Electrochemical Cascade.

Angewandte Chemie (International ed. in English)·2026
Same author

Understanding DFT Uncertainties for More Reliable Reactivity Predictions by Advancing the Analysis of Error Sources.

Journal of chemical theory and computation·2025
Same author

Counterintuitive Photochemistry of an Isolated Acridinyl Radical: ConPET via Preassembly, Solvated Electrons or a Long-Lived Excited State?

Angewandte Chemie (International ed. in English)·2025
Same author

Redox-Active Bisphosphonate-Based Viologens as Negolytes for Aqueous Organic Flow Batteries.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

Reversible covalent c-Jun N-terminal kinase inhibitors targeting a specific cysteine by precision-guided Michael-acceptor warheads.

Nature communications·2024
Same author

Illuminating the multiple Lewis acidity of triaryl-boranes <i>via</i> atropisomeric dative adducts.

Chemical science·2024

Related Experiment Video

Updated: Jul 11, 2026

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
12:11

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Published on: April 8, 2020

Computing reliable energetics for conjugate addition reactions.

Tibor András Rokob1, Andrea Hamza, Imre Pápai

  • 1Institute of Structural Chemistry, Chemical Research Center of the Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary.

Organic Letters
|September 15, 2007
PubMed
Summary

Accurate reaction energy predictions are crucial for understanding stereoselective organocatalysis. New density functionals (M05-2X, M06-2X) and SCS-MP2 method show promise for mechanistic studies.

More Related Videos

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry
16:11

Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry

Published on: June 8, 2022

Related Experiment Videos

Last Updated: Jul 11, 2026

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
12:11

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Published on: April 8, 2020

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry
16:11

Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry

Published on: June 8, 2022

Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Catalysis

Background:

  • Stereoselective organocatalysis is vital for synthesizing chiral molecules.
  • Accurate theoretical predictions are needed to understand reaction mechanisms.
  • Density functional theory (DFT) and perturbation methods are commonly used for such studies.

Purpose of the Study:

  • To evaluate the performance of various computational methods for conjugate addition reactions.
  • To identify reliable methods for predicting reaction energies in organocatalysis.
  • To explore new computational approaches for mechanistic investigations.

Main Methods:

  • Testing multiple density functionals, including B3LYP, M05-2X, and M06-2X.
  • Employing second-order perturbation treatments, specifically SCS-MP2.
  • Applying these methods to a set of conjugate addition reactions.

Main Results:

  • B3LYP significantly underestimates reaction energies.
  • M05-2X, M06-2X, and SCS-MP2 provide highly accurate reaction energy predictions.
  • The tested methods show varying degrees of accuracy for the studied reactions.

Conclusions:

  • M05-2X, M06-2X, and SCS-MP2 are promising computational tools for organocatalysis research.
  • These methods offer reliable alternatives for future mechanistic studies.
  • Accurate theoretical data can guide the development of new catalysts and reactions.