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Related Concept Videos

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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Noble Gases02:54

Noble Gases


The elements in group 18 are noble gases (helium, neon, argon, krypton, xenon, and radon). They earned the name “noble” because they were assumed to be nonreactive since they have filled valence shells. In 1962, Dr. Neil Bartlett at the University of British Columbia proved this assumption to be false.
Predicting Molecular Geometry02:27

Predicting Molecular Geometry

VSEPR Theory for Determination of Electron Pair Geometries
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Related Experiment Video

Updated: May 10, 2026

Synthesis of Triazole and Tetrazole-Functionalized Zr-Based Metal-Organic Frameworks Through Post-Synthetic Ligand Exchange
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Synthesis of Triazole and Tetrazole-Functionalized Zr-Based Metal-Organic Frameworks Through Post-Synthetic Ligand Exchange

Published on: June 23, 2023

1,2,3-triazoles: gas phase properties.

Kai Wang1, Mu Chen, Qiaoyi Wang

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08901, United States.

The Journal of Organic Chemistry
|June 29, 2013
PubMed
Summary

This study investigates the fundamental gas-phase properties of 1,2,3-triazole derivatives, including proton affinity and acidity. Findings reveal key characteristics of these important chemical compounds.

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Area of Science:

  • * Organic Chemistry: Focuses on heterocyclic compounds, specifically 1,2,3-triazoles and benzotriazoles.

Background:

  • * 1,2,3-Triazoles are increasingly vital in diverse applications.
  • * Their fundamental gas-phase properties are not well understood.
  • * Benzotriazoles and substituted 1-phenylbenzotriazoles are also examined.

Purpose of the Study:

  • * To characterize the gas-phase properties of selected 1,2,3-triazole and benzotriazole derivatives.
  • * To determine proton affinity and acidity values.
  • * To investigate tautomer prevalence in 4-phenyl-1,2,3-triazole.

Main Methods:

  • * Computational chemistry methods were employed for property calculations.
  • * Experimental measurements of proton affinity and acidity were performed.
  • * Ion-molecule reactions and H/D exchange studies were utilized.

Main Results:

  • * Computed and measured proton affinity and acidity values are reported for the first time for these species.
  • * Ion-molecule reactions and H/D exchange studies provided insights into tautomerism.
  • * The prevalence of different tautomers for 4-phenyl-1,2,3-triazole was ascertained.

Conclusions:

  • * This work provides essential gas-phase property data for 1,2,3-triazoles and related compounds.
  • * The findings contribute to a better understanding of the fundamental chemistry of these important heterocycles.
  • * The study clarifies tautomeric forms, crucial for understanding reactivity and applications.