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Related Concept Videos

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.
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.
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.
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Published on: January 19, 2016

N-Ferrocenylmethyl-2-nitro-aniline.

Oumelkheir Rahim1, Abdelhamid Khelef, Belgacem Terki

  • 1Department of Chemistry, University of Ouargla, PO Box 511, Ouargla 30000, Algeria.

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

This study details the crystal structure of a novel iron compound featuring two nearly eclipsed cyclopentadienyl (Cp) rings. A nitro-benzenamine substituent influences the molecular geometry and forms intramolecular hydrogen bonds.

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Area of Science:

  • Organometallic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Organometallic compounds with cyclopentadienyl (Cp) ligands are crucial in catalysis and materials science.
  • Understanding the structural nuances of substituted Cp complexes provides insights into their reactivity and properties.

Purpose of the Study:

  • To elucidate the crystal structure of the iron compound [Fe(C5H5)(C12H11N2O2)].
  • To analyze the geometric arrangement of the cyclopentadienyl rings and the nitro-benzenamine substituent.
  • To identify and characterize intra- and intermolecular hydrogen bonding interactions.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
  • Analysis of bond angles, dihedral angles, and torsion angles provided detailed geometric information.
  • Hydrogen bond analysis identified specific interactions within the crystal lattice.

Main Results:

  • The two cyclopentadienyl (Cp) rings in the iron complex are nearly eclipsed, with a dihedral angle of 2.54°.
  • The nitro-benzenamine group is oriented nearly perpendicular to the substituted Cp ring (torsion angle of 89.8°).
  • Intramolecular N-H⋯O and N-H⋯N hydrogen bonds were observed, along with weak intermolecular C-H⋯O hydrogen bonds.

Conclusions:

  • The crystal structure reveals a specific spatial arrangement of ligands around the iron center.
  • Intramolecular hydrogen bonding plays a significant role in stabilizing the molecular conformation.
  • Intermolecular interactions contribute to the overall crystal packing.