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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...
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Mass Spectrometry of Amines01:19

Mass Spectrometry of Amines

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In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule: a molecule with an odd number of nitrogen atoms produces a parent ion with an odd molecular weight. The remaining fragments have an even mass.
Amines undergo fragmentation through α cleavage, producing nitrogen-containing cations—iminium ions—and alkyl radicals. Mass spectra of aromatic and cyclic aliphatic amines exhibit...
4.3K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.7K
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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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.0K
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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Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.6K
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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Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O
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In Silico Partial N2 to NH3 Conversion with a Light Atom Molecule.

Stefan Mebs1

  • 1Institut für Experimentalphysik, Freie Universität Berlin, Arnimallee 14, 14195, Berlin, Germany.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|November 23, 2022
PubMed
Summary

This study introduces a novel silicon-based compound that activates nitrogen gas (N₂) for ammonia synthesis. The molecule utilizes intramolecular frustrated Lewis pairs (FLPs) to weaken the N≡N bond, enabling efficient hydrogen transfer.

Keywords:
density functional calculationsfrustrated Lewis pairsnitrogen splittingperi-substituted systemsreal-space bonding indicators

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Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O
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Area of Science:

  • Computational Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • Nitrogen fixation is crucial for ammonia production, but N₂'s inertness poses challenges.
  • Frustrated Lewis pairs (FLPs) offer a promising avenue for small molecule activation.
  • Developing efficient, light-element-based N₂ activators remains a key research goal.

Purpose of the Study:

  • To computationally investigate a novel pincer-related compound for N₂ activation.
  • To explore the mechanism of N₂ conversion into ammonia and amides using this activator.
  • To understand the role of Lewis acidity and basicity in N₂ activation.

Main Methods:

  • In silico (computational) modeling of a designed N₂-activating molecule.
  • Analysis of electronic structure and bonding in the N₂-activated complex.
  • Investigation of reaction pathways for hydrogen transfer and ammonia release.

Main Results:

  • A silyl ion-centered compound with Lewis acidic BF₂ and basic PMe₂ sites effectively binds and activates N₂.
  • The N≡N triple bond is significantly weakened (from 1.09 Å to 1.43 Å), facilitating hydride and proton addition.
  • The system enables stepwise hydrogen transfer, leading to ammonia release but also potential catalyst poisoning.

Conclusions:

  • Tetrahedral SiBP₂-constrained pockets are effective for N₂ activation via intramolecular FLPs.
  • The acid-base balance and orientation within the activator pocket are critical for success.
  • This work provides insights into designing efficient, light-element catalysts for nitrogen fixation.