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Related Concept Videos

Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

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.
Weak Acid Solutions04:02

Weak Acid Solutions

Few compounds act as strong acids. A far greater number of compounds behave as weak acids and only partially react with water, leaving a large majority of dissolved molecules in their original form and generating a relatively small amount of hydronium ions. Weak acids are commonly encountered in nature, being the substances partly responsible for the tangy taste of citrus fruits, the stinging sensation of insect bites, and the unpleasant smells associated with body odor. A familiar example of a...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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...
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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...
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...

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Lithium amide (LiNH2) under pressure.

Dasari L V K Prasad1, N W Ashcroft, Roald Hoffmann

  • 1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.

The Journal of Physical Chemistry. A
|September 18, 2012
PubMed
Summary
This summary is machine-generated.

High pressure reveals new crystal structures for lithium amide (LiNH2). Novel phases with N-H···N hydrogen bonds emerge, forming polymeric chains resistant to metallization.

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Area of Science:

  • Materials Science
  • Solid-State Chemistry
  • Computational Materials Science

Background:

  • Understanding the behavior of materials under extreme conditions is crucial for developing new technologies.
  • Lithium amide (LiNH2) is a compound with potential applications, but its high-pressure behavior is not well understood.

Purpose of the Study:

  • To predict and characterize static high-pressure crystal structures of lithium amide (LiNH2).
  • To explore the relationship between LiNH2 structure, properties, and its valence-isoelectronic analogs under pressure.

Main Methods:

  • Utilized evolutionary structure search methodologies and intuitive approaches for crystal structure prediction.
  • Performed first-principles calculations to determine structural and energetic properties.
  • Analyzed bonding, hydrogen bonding, and potential phase transitions.

Main Results:

  • Identified a competitive NaNH2 (Fddd) structure type for LiNH2 above 6 GPa.
  • Discovered three novel LiNH2 phases (P4[overline]2(1)m, P4(2)/ncm, P2(1)2(1)2(1)) with N-H···N hydrogen bonds.
  • Observed the formation of infinite polymeric zigzag chains with symmetric N···H···N hydrogen bonds in high-pressure phases (>280 GPa).
  • All predicted phases are enthalpically stable but resist metallization up to several TPa.

Conclusions:

  • High pressure induces significant structural transformations in LiNH2, leading to novel crystalline phases.
  • The formation of extended hydrogen-bonded networks is a key feature of high-pressure LiNH2.
  • LiNH2 remains an insulating material even at extreme pressures, suggesting potential for specific applications.