Azide Reactions

Azide reactions are chemical transformations involving organic or inorganic azides, compounds defined by the covalent nitrogen-rich functional group -N3, and they are important because azides support diverse synthetic and bioconjugation strategies. Their reactivity arises from the arrangement of three nitrogen atoms, which enables processes such as 1,3-dipolar cycloaddition with alkynes to form triazoles and reduction or rearrangement reactions that generate amines or isocyanates. In chemistry, azide reactions underpin copper-catalyzed and strain-promoted click chemistry, Staudinger ligations, and Curtius rearrangements. These methods enable selective molecular assembly, fluorescent labeling, polymer modification, drug development, and the construction of complex biomolecules.

Azide Reactions - Related Videos

Research

JoVE Journal - Chemistry

An Optimized Protocol for the Efficient Radiolabeling of Gold Nanoparticles by Using a 125I-labeled Azide Prosthetic Group

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Cited by 5 •

2016

A detailed procedure for the synthesis of a 125I-labeled azide and the radiolabeling of dibenzocyclooctyne (DBCO)-group-conjugated, 13-nm-sized gold nanoparticles using a copper-free click reaction is described.

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Cited by 1 •

2016

Here, we present a protocol to synthesize a complex organic compound comprised of three nonplanar polyaromatic units, assembled easily with reasonable yields.

Education

JoVE Core - Organic Chemistry

Preparation of 1° Amines: Azide Synthesis

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2023

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...

Reaction Mechanisms

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2020

Chemical reactions often occur in a stepwise fashion, involving two or more distinct reactions taking place in a sequence. A balanced equation indicates the reacting species and the product species, but it reveals no details about how the reaction occurs at the molecular level. The reaction mechanism (or reaction path) provides details regarding the precise, step-by-step process by which a reaction occurs. For instance, the decomposition of ozone appears to follow a mechanism with two steps:

Determining Order of Reaction

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2020

Rate laws describe the relationship between the rate of a chemical reaction and the concentration of its reactants. In a rate law, the rate constant k and the reaction orders are determined experimentally by observing how the rate of reaction changes as the concentrations of the reactants are changed. A common experimental approach to the determination of rate laws is the method of initial rates. This method involves measuring reaction rates for multiple experimental trials carried out using...

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