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Related Concept Videos

Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

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Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
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Batteries and Fuel Cells03:12

Batteries and Fuel Cells

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A battery is a galvanic cell that is used as a source of electrical power for specific applications. Modern batteries exist in a multitude of forms to accommodate various applications, from tiny button batteries such as those that power wristwatches to the very large batteries used to supply backup energy to municipal power grids. Some batteries are designed for single-use applications and cannot be recharged (primary cells), while others are based on conveniently reversible cell reactions that...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.3K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
2.7K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.7K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions
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Lithiated primary amine--a new material for hydrogen storage.

Juner Chen1, Hui Wu, Guotao Wu

  • 1Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P. R. China), Fax: (+86) 411-8437-9583; University of Chinese Academy of Sciences, Beijing, 100049 (P. R. China).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 17, 2014
PubMed
Summary

Researchers developed a simple ball milling method to create lithiated amines. These novel materials show potential for hydrogen storage due to their endothermic dehydrogenation, releasing hydrogen selectively.

Keywords:
dehydrogenationhydrogen storagelithiated aminesorganometallic chemistryα,β-elimination

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Area of Science:

  • Materials Science
  • Inorganic Chemistry
  • Chemical Engineering

Background:

  • Developing efficient hydrogen storage materials is crucial for advancing clean energy technologies.
  • Existing methods for synthesizing lithiated amines can be complex and inefficient.
  • Understanding dehydrogenation mechanisms is key to designing better hydrogen release systems.

Purpose of the Study:

  • To develop a facile synthesis route for crystalline lithiated amines.
  • To investigate the hydrogen storage potential of these novel materials.
  • To elucidate the mechanism of dehydrogenation in lithiated amines.

Main Methods:

  • Ball milling of primary amines with lithium hydride (LiH).
  • Thermal analysis (e.g., Differential Scanning Calorimetry) to study dehydrogenation.
  • Structural analysis and mechanistic studies, focusing on lithiated ethylenediamine (Li2EDA).

Main Results:

  • A straightforward ball milling method successfully synthesized crystalline lithiated amines.
  • Lithiated amines demonstrated endothermic dehydrogenation between 150-250°C.
  • Mechanistic studies suggested an α,β-LiH elimination pathway for selective H2 release in Li2EDA.

Conclusions:

  • The developed ball milling technique offers an efficient way to produce lithiated amine hydrogen storage materials.
  • The observed endothermic dehydrogenation highlights their potential as a new class of hydrogen storage materials.
  • The proposed α,β-LiH elimination mechanism provides insights into controlled hydrogen release.