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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.
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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
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.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

N'-(2-Hy-droxy-4-meth-oxy-benzyl-idene)-3-nitro-benzohydrazide.

Chun-Bao Tang1

  • 1Department of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
PubMed
Summary

This study details the crystal structure of a C15H13N3O3 molecule. An intramolecular hydrogen bond affects its planarity, with benzene rings forming a 11.4° dihedral angle.

Area of Science:

  • Crystallography
  • Molecular Chemistry

Background:

  • Understanding molecular conformation and intermolecular interactions is crucial in chemistry.
  • Crystal structure analysis provides detailed insights into molecular arrangement and bonding.

Purpose of the Study:

  • To determine and analyze the crystal structure of the title compound C15H13N3O3.
  • To investigate the influence of intramolecular hydrogen bonding on molecular planarity.
  • To characterize intermolecular interactions in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the molecular structure.
  • Analysis of hydrogen bonding networks, including intramolecular and intermolecular interactions.
  • Determination of key conformational parameters, such as dihedral angles between aromatic rings.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Main Results:

  • The crystal structure of C15H13N3O3 was successfully determined.
  • An intramolecular O-H⋯N hydrogen bond was identified, impacting the molecule's conformation.
  • A dihedral angle of 11.4(3)° between the benzene rings was measured, indicating a near-planar conformation.
  • Intermolecular N-H⋯O hydrogen bonds were observed, leading to the formation of one-dimensional chains along the [101] direction.

Conclusions:

  • The crystal packing is significantly influenced by both intra- and intermolecular hydrogen bonding.
  • The identified hydrogen bonds play a key role in stabilizing the observed molecular conformation and the overall crystal structure.
  • This structural data provides a foundation for further studies on the properties and potential applications of this compound.