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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.2K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

9.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
9.8K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

11.8K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
11.8K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

13.9K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
13.9K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.8K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.8K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

8.4K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
8.4K

You might also read

Related Articles

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

Sort by
Same author

8-Aminoquinoline Pendant Ligand-Driven Proton Shuttling in Copper Electrocatalysis for Enhanced Proton Reduction into Hydrogen Gas.

Inorganic chemistry·2026
Same author

Dynamic Kinetic Resolution Enabled Synthesis of Planar and Central Chiral Ferrocenes.

Organic letters·2026
Same author

Monodentate Transient Directing Group Enabled Distal C─H Bond Functionalization in Ferrocenecarboxaldehyde.

Chemistry, an Asian journal·2026
Same author

Visible-Light-Mediated C(sp<sup>3</sup>)-Se Coupling: Synthesis of GPx-Mimic Unsymmetrical Aryl-Secondary Alkyl Selenoether Antioxidants.

The Journal of organic chemistry·2026
Same author

Native-carboxylate-assisted enantioselective C-H annulations with allenes and 1,3-dienes on ferrocene.

Chemical communications (Cambridge, England)·2025
Same author

Pd-Catalyzed Enantioselective Double C-H Activation and Transmetalation: Synthesis of 2-Heteroaryl/aryl-Ferrocenealdehydes.

Organic letters·2025

Related Experiment Video

Updated: Jun 1, 2025

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

3.5K

Organoselenium Ligand Enabled Selective Electron Tuning for Switchable Hydrogen Evolution Reaction.

Svastik Jaiswal1, Raushan Kumar Jha1, Devendra Parganiha1

  • 1Department of Chemistry, Indian Institution of Science Education and Research, Bhopal By-pass Road, Bhauri, Bhopal, Madhya Pradesh, 462066, India.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 20, 2025
PubMed
Summary

Nickel selenoether electrocatalysts offer tunable reaction centers for hydrogen evolution reaction (HER). Ligand-centered pathways show high efficiency, while metal-centered pathways provide excellent selectivity, revealing crucial electronic effects.

Keywords:
ElectrocatalystsElectronic tuningHydrogen evolution reactionNickel selenoetherSwitchable reaction

More Related Videos

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

8.3K
Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
10:01

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase

Published on: December 4, 2017

12.2K

Related Experiment Videos

Last Updated: Jun 1, 2025

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

3.5K
Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

8.3K
Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
10:01

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase

Published on: December 4, 2017

12.2K

Area of Science:

  • * Inorganic Chemistry
  • * Electrochemistry
  • * Catalysis

Background:

  • * Understanding metal complex electronic structures is key for advancing hydrogen evolution reaction (HER) catalysis.
  • * The precise role of metal and ligand electronic effects in modulating HER reaction centers remains incompletely understood.

Purpose of the Study:

  • * To investigate nickel selenoether electrocatalysts with tunable reaction centers for HER.
  • * To analyze the electronic modulation of metal and ligand centers in HER catalysis.

Main Methods:

  • * Synthesis and electrochemical characterization of nickel selenoether electrocatalysts.
  • * Kinetic isotopic effect (KIE) studies using deuterated acetic acid (CD3CO2D).
  • * Electron Paramagnetic Resonance (EPR) spectroscopy and Density Functional Theory (DFT) computations.

Main Results:

  • * Nickel selenoether electrocatalysts exhibited tunable HER pathways: ligand-centered (14000 s⁻¹, 93% F.E.) and metal-centered (2110 s⁻¹, 98% F.E.).
  • * KIE values (0.49 and 13.01) and EPR studies confirmed distinct metal-centered and ligand-centered radical mechanisms.
  • * DFT and electrochemical studies highlighted the selenoether ligand's electron reservoir role in dictating reaction pathways.

Conclusions:

  • * Selenoether ligands in nickel complexes can effectively tune reaction centers for highly efficient and selective HER.
  • * The electronic density of the ligand is critical for controlling HER mechanisms, offering new avenues for catalyst design.