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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Related Experiment Video

Updated: Oct 17, 2025

Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers
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Nitrogen-Based Linkers with a Mesitylene Core: Synthesis and Characterization.

Lucian Gabriel Bahrin1, Alina Nicolescu1, Sergiu Shova1

  • 1Intelcentre, Petru Poni Institute of Macromolecular Chemistry, Romanian Academy, 41A Aleea Grigore Ghica Voda, 700487 Iasi, Romania.

Molecules (Basel, Switzerland)
|October 13, 2021
PubMed
Summary

Researchers synthesized novel nitrogen-containing linkers based on a mesitylene core for potential use in metal-organic frameworks (MOFs). These linkers, featuring nitrile and triazole groups, show promise for advanced material design.

Keywords:
1,2,3-triazoleC-C couplingcycloaddition reactiontetrazoletritopic organic linker

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Mesitylene serves as a versatile core for constructing complex molecular architectures.
  • Nitrogen-containing organic linkers are crucial building blocks for designing porous materials like metal-organic frameworks (MOFs).
  • Developing new tritopic linkers with specific functionalities is essential for expanding the scope of MOF applications.

Purpose of the Study:

  • To synthesize and characterize novel tritopic nitrogen-containing linkers with nitrile and tetrazole functionalities.
  • To explore the synthetic pathways for creating diverse linker structures based on a mesitylene scaffold.
  • To demonstrate the utility of these new linkers in constructing metal-organic frameworks.

Main Methods:

  • Suzuki, Sonogashira, and Heck coupling reactions were employed for linker synthesis.
  • Cycloaddition reactions, including sodium azide addition to nitriles and Huisgen cycloaddition, were utilized to form tetrazole and triazole moieties.
  • A Corey-Fuchs reaction sequence was used to prepare alkyne intermediates.
  • An Ag-based metal-organic framework was constructed using one of the synthesized nitrile-containing linkers as a proof of concept.

Main Results:

  • Seven new tritopic nitrogen-containing linkers were successfully synthesized.
  • Three linkers featuring nitrile groups and three featuring tetrazol-5-yl moieties were obtained.
  • A linker with three 1,2,3-triazol-4-yl moieties was synthesized.
  • The successful construction of an Ag-based MOF using a nitrile linker demonstrated the practical applicability of these compounds.

Conclusions:

  • The developed synthetic strategies provide access to a range of novel tritopic nitrogen-containing linkers.
  • These linkers are suitable for the construction of metal-organic frameworks.
  • The study highlights the potential of these new materials in MOF design and applications.