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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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.
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...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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.

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Related Experiment Video

Updated: Jul 8, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Three 4,7-diaryl-2-ethylsulfanylpyrazolo[1,5-a][1,3,5]triazines.

Henry Insuasty1, Paola Mier, Gina Suarez

  • 1Departamento de Química, Universidad de Nariño, Cuidad Universitaria Torobajo, AA 1175 Pasto, Colombia.

Acta Crystallographica. Section C, Crystal Structure Communications
|January 25, 2008
PubMed
Summary

This study details the molecular structures of three pyrazolo[1,5-a][1,3,5]triazine compounds. Analysis reveals aromatic delocalization in pyrazole rings and distinct ethylsulfanyl substituent conformations, with specific compounds forming dimers via pi-stacking.

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

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Published on: January 3, 2018

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
05:07

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

Published on: June 23, 2019

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure Analysis

Background:

  • Pyrazolo[1,5-a][1,3,5]triazine derivatives are of interest due to their fused heterocyclic structure.
  • Understanding their molecular dimensions and intermolecular interactions is crucial for predicting material properties.

Purpose of the Study:

  • To elucidate the crystal structures and molecular conformations of three novel pyrazolo[1,5-a][1,3,5]triazine derivatives.
  • To investigate the presence of aromatic delocalization and intermolecular interactions within these compounds.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular dimensions.
  • Analysis of crystal packing to identify hydrogen bonding and other non-covalent interactions.

Main Results:

  • The molecular structures of three compounds (I, II, and III) were determined, showing evidence of aromatic delocalization in the pyrazole rings.
  • Distinct conformations were observed for the ethylsulfanyl substituents across the three compounds.
  • No hydrogen bonds were found; however, compounds (II) and (III) exhibited centrosymmetric dimer formation through pi-stacking interactions.

Conclusions:

  • The crystal structures confirm aromatic character within the pyrazole moieties of these triazine derivatives.
  • The variability in ethylsulfanyl group conformations highlights conformational flexibility.
  • Pi-stacking interactions play a significant role in the solid-state assembly of certain derivatives.