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Related Concept Videos

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...
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 II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
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.
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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VSEPR Theory and the Basic Shapes

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Related Experiment Video

Updated: Jun 8, 2026

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

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The first supraicosahedral bis(heteroborane).

David Ellis1, Georgina M Rosair, Alan J Welch

  • 1Department of Chemistry, Heriot-Watt University, Edinburgh, UK EH14 4AS. a.j.welch@hw.ac.uk

Chemical Communications (Cambridge, England)
|September 11, 2010
PubMed
Summary

Researchers synthesized the first supraicosahedral bis(heteroborane) molecules. Structural analysis revealed these novel compounds are internally crowded, existing as racemic and meso diastereoisomers.

Area of Science:

  • * Inorganic Chemistry
  • * Organometallic Chemistry
  • * Materials Science

Background:

  • * Heteroboranes are cage-like boron hydride clusters containing heteroatoms.
  • * Supraicosahedral clusters represent a structural expansion beyond the typical icosahedral framework.
  • * Bis(heteroboranes) involve two linked heteroborane units, offering potential for complex structures.

Purpose of the Study:

  • * To synthesize and characterize the first example of a supraicosahedral bis(heteroborane).
  • * To investigate the structural implications of linking two closo-cobaltadicarbadodecaborane units.
  • * To explore the stereochemistry and molecular crowding in these novel compounds.

Main Methods:

  • * Synthesis of the target bis(heteroborane) via a coupling reaction.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

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  • * Characterization using spectroscopic techniques (e.g., NMR).
  • * X-ray crystallography for detailed molecular structure determination.

    • Main Results:

    • * Successful synthesis of 1-(4'-Cp-4',1',6'-closo-CoC(2)B(10)H(11))-4-Cp-4,1,6-closo-CoC(2)B(10)H(11).
    • * The compound was obtained as a mixture of racemic and meso diastereoisomers.
    • * Structural analysis confirmed significant internal crowding within the supraicosahedral framework.

    Conclusions:

    • * The first supraicosahedral bis(heteroborane) has been synthesized, expanding the known chemistry of boron clusters.
    • * The linked closo-cobaltadicarbadodecaborane units lead to sterically hindered molecular architectures.
    • * This work provides a foundation for exploring more complex, crowded polyhedral cluster compounds.