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Related Concept Videos

Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

2.6K
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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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.4K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.4K
Structure of Amines01:19

Structure of Amines

2.5K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
2.5K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.8K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
3.8K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.4K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.4K

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An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
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Fragmentation Considerations Using Amidoamine Oxide Homologs.

Atsushi Yamamoto1,2, Naoji Tokai3, Rie Kakehashi3

  • 1Faculty of Environment, Tottori University of Environmental Studies, 1-1-1 Wakabadaikita, Tottori, Tottori 689-1111, Japan.

Mass Spectrometry (Tokyo, Japan)
|December 10, 2024
PubMed
Summary

This study analyzed novel amidoamine oxide hydrogelators using mass spectrometry. Characteristic fragmentation patterns were identified, aiding in the structural elucidation of these amide compounds.

Keywords:
amidoamine oxidechain-length dependence of fragmentationstructural elucidation

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Area of Science:

  • Analytical Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Amidoamine oxides are novel hydrogelators with potential applications in polar solvents.
  • Accurate structural elucidation is crucial for understanding compound properties and developing new materials.

Purpose of the Study:

  • To identify characteristic fragment patterns of 10 novel amidoamine oxide compounds using high-resolution mass spectrometry.
  • To explore the utility of low-intensity fragment peaks in the structural analysis of similar amide compounds.

Main Methods:

  • Electrospray ionization (ESI) and hybrid tandem mass spectrometry were employed.
  • MS1 and MS2 spectra were acquired in positive and negative ion modes across six collision energy levels.
  • Methanol solutions of the compounds were analyzed.

Main Results:

  • Distinct chain-length-dependent fragmentation patterns were observed for the amidoamine oxide compounds.
  • Low-intensity fragment peaks were found to provide critical structural information, especially for structurally similar compounds.
  • Challenges in balancing informative low-intensity peaks with spectral database matching were highlighted.

Conclusions:

  • Mass spectrometry, particularly when combined with separation techniques like liquid chromatography, can effectively elucidate the structures of unknown amide compounds.
  • Further development of algorithms for interpreting low-intensity peaks is recommended for improved compound identification in complex mixtures.
  • This research contributes to mass spectrometry and structural chemistry, with implications for hydrogelator development.