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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.
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.
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.
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 with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

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Bis[4-(dimethyl-amino)phen-yl]diazene oxide.

Graeme J Gainsford1, M Delower H Bhuiyan, Andrew J Kay

  • 1Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

This study details the crystal structure of a C(16)H(20)N(4)O compound, revealing six independent molecules in its asymmetric unit. The structure exhibits a unique modulation, with disordered molecules influencing crystal symmetry and cohesion through C-H⋯O interactions.

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

Published on: July 17, 2020

Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Molecular structure determination

Background:

  • Understanding the precise arrangement of molecules in a crystal lattice is fundamental to predicting material properties.
  • Crystal structures can exhibit complex modulations and disorder, challenging traditional symmetry descriptions.
  • Intermolecular interactions, such as hydrogen bonds, play a crucial role in stabilizing crystal structures.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C(16)H(20)N(4)O.
  • To characterize the nature of molecular disorder and its impact on the unit cell.
  • To identify the key intermolecular interactions responsible for structural integrity.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
  • The crystal structure was refined, accounting for the presence of multiple disordered molecular orientations.
  • Analysis of non-covalent interactions, specifically C-H⋯O hydrogen bonds, was performed.

Main Results:

  • The asymmetric unit contains six independent, approximately planar molecules of C(16)H(20)N(4)O.
  • The structure is described as a commensurate modulation of a P2(1)/c parent lattice.
  • Two sets of disordered molecules occupy similar positions, with site occupancy factors of approximately 0.72/0.28 and 0.67/0.33, preventing the attainment of a c-glide plane.
  • C-H⋯O interactions were identified as the primary forces providing structural cohesion.

Conclusions:

  • The crystal structure of C(16)H(20)N(4)O is characterized by significant molecular disorder and a modulated symmetry.
  • The observed disorder and specific intermolecular interactions dictate the overall structural stability and packing.
  • This detailed structural analysis provides a foundation for further investigations into the compound's physical and chemical properties.