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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

7.4K
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.
7.4K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.1K
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.
3.1K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.9K
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.
4.9K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.5K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.5K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.3K
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.
4.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.6K
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...
3.6K

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Related Experiment Videos

(E)-2-(2,4-Dihydroxy-benzyl-ideneamino)benzonitrile.

Ting Liu1

  • 1Biology and Chemistry Department, Nanchang University College of Science and Technology, Nanchang 330029, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study reveals the phenol-imine tautomeric form of a C(14)H(10)N(2)O(2) compound. Intramolecular hydrogen bonding stabilizes its structure, with dimers formed via intermolecular interactions in the crystal lattice.

Related Experiment Videos

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
  • Phenol-imine tautomerism influences the physicochemical properties of organic compounds.
  • Hydrogen bonding plays a key role in stabilizing molecular structures and directing crystal packing.

Purpose of the Study:

  • To elucidate the tautomeric form and detailed molecular conformation of the title compound.
  • To investigate the role of intramolecular and intermolecular hydrogen bonding in the crystal structure.
  • To analyze the dihedral angle between the benzene rings and its impact on molecular geometry.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
  • Analysis of bond lengths, bond angles, and hydrogen bonding interactions.
  • Computational methods may be used to complement experimental findings (if applicable).

Main Results:

  • The title compound, C(14)H(10)N(2)O(2), crystallizes in the phenol-imine tautomeric form.
  • A significant intramolecular O-H⋯N hydrogen bond stabilizes the molecular conformation.
  • The dihedral angle between the two benzene rings is determined to be 13.84°.
  • Intermolecular C-H⋯O and O-H⋯N hydrogen bonds link molecules into centrosymmetric dimers in the crystal.

Conclusions:

  • The phenol-imine tautomer is the predominant form in the solid state.
  • Intramolecular hydrogen bonding is a key stabilizing factor for the observed molecular conformation.
  • The crystal structure is characterized by dimer formation through a network of intermolecular hydrogen bonds.