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

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Molecular Orbital Theory II03:51

Molecular Orbital Theory II

Molecular Orbital Energy Diagrams
VSEPR Theory and the Basic Shapes02:52

VSEPR Theory and the Basic Shapes

Overview of VSEPR Theory

You might also read

Related Articles

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

Sort by
Same author

The Critical Role of Nanoparticle Geometry in Turnover Frequency Calculation.

ACS measurement science au·2025
Same author

Deep Eutectic Solvents Formed by Complex Hydrides: A New Class of Hydrogen-Rich Liquid.

Advanced materials (Deerfield Beach, Fla.)·2025
Same author

Rational design of a methanation reactor by neutron imaging.

Physical chemistry chemical physics : PCCP·2025
Same author

Functionalized Phenyl Methanaminium Salts Provide Highly Stable Perovskite Solar Cells.

ACS applied materials & interfaces·2025
Same author

Assessment of fine-tuned large language models for real-world chemistry and material science applications.

Chemical science·2024
Same author

Laser-Stimulated Desorption of Hydrogen in Palladium for Dynamic Hydrogen Sorption Microanalysis.

Analytical chemistry·2024

Related Experiment Video

Updated: May 17, 2026

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
09:05

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

Diborane release and structure distortion in borohydrides.

Elsa Callini1, Andreas Borgschulte, Anibal Javier Ramirez-Cuesta

  • 1Empa, Swiss Federal Laboratories for Materials Testing and Research, Hydrogen & Energy, CH-8600 Dübendorf, Switzerland.

Dalton Transactions (Cambridge, England : 2003)
|October 11, 2012
PubMed
Summary
This summary is machine-generated.

Diborane release during borohydride decomposition is linked to cation electronegativity and anion distortion. A new model explains diborane formation via BH(2)(δ+) and BH(4)(δ-) recombination, supported by mass spectroscopy.

More Related Videos

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions
06:32

A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions

Published on: August 17, 2016

Related Experiment Videos

Last Updated: May 17, 2026

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
09:05

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions
06:32

A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions

Published on: August 17, 2016

Area of Science:

  • Materials Science
  • Inorganic Chemistry
  • Chemical Engineering

Background:

  • Hydrogen desorption from borohydrides often releases diborane.
  • Diborane byproduct formation scales inversely with borohydride stability.
  • Cation electronegativity influences borohydride stability and decomposition pathways.

Purpose of the Study:

  • To present a model explaining diborane formation during borohydride decomposition.
  • To correlate anion distortion with diborane release.
  • To investigate the decomposition mechanisms of LiZn(2)(BH(4))(5) and LiBH(4).

Main Methods:

  • Theoretical modeling based on symmetric and asymmetric assembly of B(2)H(6) units.
  • Analysis of anion distortion using vibrational spectroscopy (Badger's rule).
  • Ultra-high vacuum (UHV) mass spectroscopy measurements.

Main Results:

  • A model is proposed where diborane forms from BH(2)(δ+) and BH(4)(δ-) recombination on the surface.
  • Anion distortion, measured by vibrational mode energy differences, correlates with diborane release.
  • UHV mass spectroscopy confirms the model and differentiates decomposition in stable vs. unstable borohydrides.

Conclusions:

  • The degree of cation ionization dictates BH(4)(-) anion distortion, influencing diborane byproduct formation.
  • The presented model provides a mechanistic understanding of diborane release from borohydrides.
  • Sublimation and decomposition are competing processes for borohydrides under UHV conditions.