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

E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

10.7K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
10.7K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

15.8K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
15.8K
SN1 Reaction: Mechanism02:25

SN1 Reaction: Mechanism

12.4K
Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism. 
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a...
12.4K
π Electron Effects on Chemical Shift: Overview01:27

π Electron Effects on Chemical Shift: Overview

1.1K
An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0,...
1.1K
SN1 Reaction: Kinetics02:05

SN1 Reaction: Kinetics

8.1K
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...
8.1K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.1K
Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
1.1K

You might also read

Related Articles

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

Sort by
Same author

Crystal-environment control of excited-state reaction branching in 5-chloro-<i>N</i>-salicylideneaniline.

Physical chemistry chemical physics : PCCP·2026
Same author

Spin-Projected Divide-and-Conquer Unrestricted Self-Consistent Field: Practical Linear-Scaling Approaches for Static Correlation.

Journal of chemical theory and computation·2026
Same author

RETRACTED: Novel target genes responsive to the anti-growth activity of triptolide in endometrial and ovarian cancer cells.

Cancer letters·2026
Same author

Symposium Report: Stakeholders' Perspectives on Phase 1 Trials in Japanese Prior to Multi-Regional Clinical Trials and Future Pathways.

Clinical pharmacology and therapeutics·2026
Same author

Trophic Role of the Tetrodotoxin-Bearing Flatworm Plancera multitentaculata in the Marine Food Web.

Marine biotechnology (New York, N.Y.)·2026
Same author

Ground-and excited-state fragmentation dynamics of doubly ionized OCS: A theoretical study.

The Journal of chemical physics·2025

Related Experiment Video

Updated: Sep 12, 2025

Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
08:24

Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling

Published on: November 11, 2008

16.5K

Tracking electron motion driving the Suzuki-Miyaura cross-coupling reaction.

Noriyuki Takai1, Takuro Tsutsumi2, Tetsuya Taketsugu2,3

  • 1Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-8628, Japan.

Physical Chemistry Chemical Physics : PCCP
|August 5, 2025
PubMed
Summary

Reactive orbital energy theory (ROET) reveals electron motion in Suzuki-Miyaura cross-coupling. The boronate mechanism is favored due to lower activation energy and simpler pathway, aligning with experimental data.

More Related Videos

Single-Molecule F&#246;rster Resonance Energy Transfer Methods for Real-Time Investigation of the Holliday Junction Resolution by GEN1
11:27

Single-Molecule Förster Resonance Energy Transfer Methods for Real-Time Investigation of the Holliday Junction Resolution by GEN1

Published on: September 18, 2019

9.6K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.6K

Related Experiment Videos

Last Updated: Sep 12, 2025

Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
08:24

Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling

Published on: November 11, 2008

16.5K
Single-Molecule F&#246;rster Resonance Energy Transfer Methods for Real-Time Investigation of the Holliday Junction Resolution by GEN1
11:27

Single-Molecule Förster Resonance Energy Transfer Methods for Real-Time Investigation of the Holliday Junction Resolution by GEN1

Published on: September 18, 2019

9.6K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.6K

Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Reaction Mechanisms

Background:

  • The Suzuki-Miyaura cross-coupling is a vital reaction in organic synthesis.
  • Understanding the electron dynamics during transmetalation is crucial for reaction optimization.

Purpose of the Study:

  • To elucidate the electron motion driving the transmetalation step in Suzuki-Miyaura cross-coupling.
  • To compare the mechanistic pathways of boronate and oxo-palladium mechanisms using ROET.

Main Methods:

  • Computational investigation using intrinsic reaction coordinate (IRC) calculations.
  • Analysis of electron motion via reactive orbital energy theory (ROET).

Main Results:

  • The boronate mechanism exhibits a lower activation barrier and a simpler reaction pathway compared to the oxo-palladium mechanism.
  • ROET analysis demonstrated electron motion patterns consistent with experimental observations.
  • The electronic roles of organoboronic acid and ancillary ligands were clarified by ROET.

Conclusions:

  • ROET offers a novel perspective for understanding electron motion in metal-catalyzed reactions.
  • The findings support the boronate mechanism as the predominant pathway in this Suzuki-Miyaura coupling.
  • ROET provides valuable insights into the fundamental electronic processes governing catalytic reactions.