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Related Concept Videos

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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...
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Stability of Substituted Cyclohexanes02:30

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
13.3K
Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

2.9K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

1.9K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Updated: May 1, 2026

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Computational study on the vinyl azide decomposition.

Darío J R Duarte1, Margarida S Miranda, Joaquim C G Esteves da Silva

  • 1Laboratorio de Estructura Molecular y Propiedades, Área de Quı́mica Fı́sica-Departamento de Quı́mica, Facultad de Ciencias Exactas y Naturales y Agrimensura, Universidad Nacional del Nordeste , Avenida Libertad 5460, 3400 Corrientes, Argentina.

The Journal of Physical Chemistry. A
|April 15, 2014
PubMed
Summary
This summary is machine-generated.

Vinyl azide decomposition pathways were computationally studied. The s-cis conformer yields ketenimine in one step, while the s-trans conformer forms acetonitrile via a two-step process involving vinyl nitrene intermediates.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Organic Chemistry

Background:

  • Vinyl azide is an energetic molecule with potential applications.
  • Understanding its decomposition pathways is crucial for safety and reaction design.
  • Vinyl nitrenes are key intermediates in azide decomposition.

Purpose of the Study:

  • To elucidate the decomposition mechanisms of vinyl azide (CH2CHN3).
  • To investigate the electronic structure and topological properties of vinyl nitrene intermediates.
  • To understand the electron redistribution during vinyl azide decomposition.

Main Methods:

  • Electronic structure calculations.
  • Quantum Theory of Atoms in Molecules (QTAIM) analysis.
  • Topological analysis of electron charge density and Laplacian function.

Main Results:

  • The s-cis conformer of vinyl azide decomposes to ketenimine in a single step.
  • The s-trans conformer decomposes to acetonitrile in a two-step process.
  • Triplet vinyl nitrene acts as a monodentate Lewis base, while singlet vinyl nitrene acts as a bidentate Lewis base.

Conclusions:

  • Distinct decomposition pathways exist for s-cis and s-trans vinyl azide conformers.
  • The electronic and topological properties of vinyl nitrenes dictate their reactivity as Lewis bases.
  • Computational methods provide detailed insights into complex chemical reaction mechanisms.