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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.
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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.
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...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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.
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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(E)-2-Acetyl-pyrazine 4-nitro-phenyl-hydrazone.

Shang Shan1, Yu-Liang Tian, Shan-Heng Wang

  • 1College of Chemical Engineering and Materials Science, Zhejiang University of Technology, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary
This summary is machine-generated.

The crystal structure of a C(12)H(11)N(5)O(2) compound reveals molecules in an E configuration. Adjacent molecules exhibit pi-pi stacking and hydrogen bonding, influencing crystal packing.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding molecular interactions is crucial for designing materials with specific properties.
  • Crystal engineering relies on predicting and controlling intermolecular forces.
  • The study of organic compounds with fused ring systems offers insights into π-π stacking and hydrogen bonding.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C(12)H(11)N(5)O(2).
  • To investigate the intermolecular interactions, including π-π stacking and hydrogen bonding, within the crystal lattice.
  • To characterize the molecular conformation and its influence on crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
  • Analysis of the crystal structure involved identifying and quantifying intermolecular contacts.
  • Geometric parameters such as bond lengths, bond angles, and non-bonded distances were analyzed.

Main Results:

  • The title compound, C(12)H(11)N(5)O(2), crystallizes with molecules adopting an E configuration.
  • Significant π-π stacking interactions were observed between adjacent benzene rings (3.413 Å) and pyrazine rings (3.430 Å).
  • The crystal structure is further stabilized by N-H⋯N and C-H⋯O hydrogen bonds.

Conclusions:

  • The molecular structure and conformation are dictated by the E configuration around the N=C double bond.
  • Intermolecular π-π stacking and hydrogen bonding play a key role in the self-assembly and stability of the crystal structure.
  • The findings contribute to the understanding of structure-property relationships in organic crystalline materials.