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Rate-Determining Steps

Rate-Determining Steps

Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...

Nitriles to Ketones: Grignard Reaction

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Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...

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Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

New mechanistic interpretations for nitrone reactivity.

Pedro Merino¹, Tomás Tejero, Ignacio Delso

¹Instituto de Biocomputación y Fisica de Sistemas Complejos (BIFI), Universidad de Zaragoza, Campus San Francisco, 50009 Zaragoza, Aragón, Spain. pmerino@unizar.es.

Organic & Biomolecular Chemistry

|March 23, 2017

Summary

This summary is machine-generated.

This study uses electron localization function (ELF) to analyze nitrone reactivity in cycloadditions. It reveals sequential bond formation, challenging classical mechanistic views of these important reactions.

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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

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Published on: September 25, 2017

Area of Science:

Organic Chemistry
Theoretical Chemistry

Background:

Nitrone reactivity is crucial in organic synthesis.
Classical mechanistic studies often simplify complex reaction pathways.

Purpose of the Study:

To re-evaluate nitrone reactivity using a topological perspective.
To investigate bond reorganization during cycloaddition and related reactions.

Main Methods:

Utilized the electron localization function (ELF) to analyze reaction pathways.
Applied computational methods to study bond formation dynamics.

Main Results:

Demonstrated sequential bond formation in several nitrone-mediated reactions.
Identified unexpected mechanistic features in 1,3-dipolar cycloadditions and Mannich-type reactions.
Highlighted limitations of classical mechanistic interpretations.

Conclusions:

The topological approach offers deeper insights into nitrone reaction mechanisms.
Sequential bond formation is a key feature often overlooked.
Revisiting reactions with advanced computational tools can uncover novel mechanistic details.