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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

Study of boron-nitrogen dative bonds using azetidine inversion dynamics.

Cam Thuy Hoang1, Ivan Prokes, Guy J Clarkson

  • 1Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK.

Chemical Communications (Cambridge, England)
|February 21, 2013
PubMed
Summary

This study introduces a new method to measure the strength of boron-nitrogen dative bonds. Researchers quantified nitrogen inversion barriers in azetidines, providing insights into B-N bond characteristics.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • Boron-nitrogen (B-N) dative bonds are crucial in various chemical applications.
  • Understanding the factors influencing B-N bond strength is essential for designing novel materials and catalysts.
  • Azetidines offer a constrained framework for studying intramolecular interactions.

Purpose of the Study:

  • To develop and apply a novel method for quantifying the strength of B-N dative bonds.
  • To investigate the relationship between nitrogen inversion barriers and B-N dative bond strength.
  • To explore the utility of variable temperature Nuclear Magnetic Resonance (VT-NMR) spectroscopy in this context.

Main Methods:

  • Synthesis of azetidine derivatives functionalized with boronate esters.
  • Quantification of nitrogen inversion activation parameters using VT-NMR spectroscopy.
  • Correlation of NMR data with results from (11)B NMR, X-ray crystallography, and MP2 computational calculations.

Main Results:

  • Successful quantification of activation parameters for nitrogen inversion in the studied azetidines.
  • Demonstrated correlation between measured inversion barriers and B-N dative bond characteristics.
  • Validation of the developed method through complementary spectroscopic and crystallographic techniques.

Conclusions:

  • The reported method provides a reliable approach to probe B-N dative bond strength.
  • Nitrogen inversion barriers serve as effective indicators of B-N dative bond strength in these systems.
  • The study highlights the synergy between experimental and computational methods in understanding chemical bonding.