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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.
Lewis Acids and Bases02:16

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This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
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Lewis Acids and Bases

In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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.
Preparation of Alcohols via Addition Reactions02:15

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Updated: Jun 20, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Published on: March 24, 2018

Ammonia borane hydrogen release in ionic liquids.

Daniel W Himmelberger1, Laif R Alden, Martin E Bluhm

  • 1Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

Inorganic Chemistry
|September 23, 2009
PubMed
Summary
This summary is machine-generated.

Ionic liquids significantly accelerate hydrogen release from ammonia borane (AB), a key hydrogen storage material. This advancement overcomes limitations of solid-state reactions, enabling faster and more efficient hydrogen utilization.

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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Electrochemistry

Background:

  • Ammonia borane (AB) is a high-capacity hydrogen storage material with potential for clean energy applications.
  • Solid-state hydrogen release from AB often suffers from slow kinetics and long induction periods.
  • Ionic liquids offer unique solvation properties that can influence chemical reaction pathways.

Purpose of the Study:

  • To investigate the effect of ionic liquids on the rate and extent of hydrogen (H2) release from ammonia borane (AB).
  • To compare the performance of AB in ionic liquid solutions with traditional solid-state reactions.
  • To elucidate the mechanism of enhanced H2 release in the presence of ionic liquids.

Main Methods:

  • Hydrogen release kinetics studies of ammonia borane in 1-butyl-3-methylimidazolium chloride (bmimCl) ionic liquid solutions at various temperatures and compositions.
  • Comparison with solid-state ammonia borane reactions under identical temperature conditions.
  • Solid-state and solution (11)B NMR spectroscopy to study reaction intermediates and mechanisms.

Main Results:

  • Ionic liquid solutions dramatically reduced or eliminated the induction period for H2 release from AB.
  • Hydrogen release rates were significantly enhanced in AB/bmimCl mixtures compared to solid-state reactions.
  • A 50:50-wt % AB/bmimCl mixture at 110°C released 2.2 H2-equiv in only 20 minutes.
  • An 80:20-wt % AB/bmimCl system achieved 11.4 material-weight percent H2 release.
  • (11)B NMR studies supported a mechanism involving ionic liquid-promoted conversion to DADB and subsequent dehydrocoupling.

Conclusions:

  • Ionic liquids are effective catalysts for enhancing the rate and extent of hydrogen release from ammonia borane.
  • The use of ionic liquids presents a promising strategy for improving hydrogen storage and release technologies.
  • The proposed mechanism involving DADB formation and dehydrocoupling provides insight into optimizing AB-based hydrogen storage systems.