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EDTA: Auxiliary Complexing Reagents

EDTA: Auxiliary Complexing Reagents

EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...

Acid Halides to Ketones: Gilman Reagent

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...

Reaction Mechanisms

Reaction Mechanisms

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

Determining Order of Reaction

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...

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.

Reaction Yield

Reaction Yield

The theoretical yield of a reaction is the amount of product estimated to form based on the stoichiometry of the balanced chemical equation. The theoretical yield assumes the complete conversion of the limiting reactant into the desired product. The amount of product that is obtained by performing the reaction is called the actual yield, and it may be less than or (very rarely) equal to the theoretical yield.

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Updated: Feb 11, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Constructing New Bioorthogonal Reagents and Reactions.

R David Row, Jennifer A Prescher

Accounts of Chemical Research

|May 5, 2018

Summary

Researchers developed novel, small bioorthogonal reagents like cyclopropenes, triazines, and cyclopropenones for enhanced biological studies. These tools offer improved stability and selectivity, enabling new discoveries in biomolecule research.

Area of Science:

Chemical Biology
Organic Chemistry
Biochemistry

Background:

Bioorthogonal reagents are crucial chemical tools for understanding biomolecules and living systems.
Existing bioorthogonal reagents face limitations such as large size, insufficient stability, and cross-reactivity.

Purpose of the Study:

To address limitations in the bioorthogonal toolbox by developing novel, small, and tunable reagents.
To explore the potential of cyclopropenes, triazines, and cyclopropenones as next-generation bioorthogonal tools.

Main Methods:

Leveraging natural product structures for bioorthogonal probe design, ensuring metabolic stability.
Utilizing computational analyses and mechanistic studies to fine-tune reagent reactivity and stability.
Developing mutually orthogonal reactions for simultaneous use in complex biological systems.

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Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry

Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry

Published on: February 4, 2017

Genetic Encoding of a Non-Canonical Amino Acid for the Generation of Antibody-Drug Conjugates Through a Fast Bioorthogonal Reaction

Genetic Encoding of a Non-Canonical Amino Acid for the Generation of Antibody-Drug Conjugates Through a Fast Bioorthogonal Reaction

Published on: September 14, 2018

Related Experiment Videos

Last Updated: Feb 11, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry

Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry

Published on: February 4, 2017

Genetic Encoding of a Non-Canonical Amino Acid for the Generation of Antibody-Drug Conjugates Through a Fast Bioorthogonal Reaction

Genetic Encoding of a Non-Canonical Amino Acid for the Generation of Antibody-Drug Conjugates Through a Fast Bioorthogonal Reaction

Published on: September 14, 2018

Main Results:

Developed small, tunable bioorthogonal reagents including cyclopropenes, triazines, and cyclopropenones.
Identified reagents with varying selectivity and robustness, suitable for both in vitro and in vivo applications.
Established strategies for creating mechanistically distinct and biocompatible bioorthogonal reactions.

Conclusions:

Novel bioorthogonal reagents derived from natural products offer improved performance for biological research.
Fine-tuning reagent properties is essential for expanding their application in live cells and organisms.
Continued development of mechanistically diverse bioorthogonal reactions is vital for advancing biomolecular studies.