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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.
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.
UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
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...

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Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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(E)-1-(2-Nitro-ethen-yl)naphthalene.

Lin-Hai Jing1

  • 1School of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a C(12)H(9)NO(2) molecule, revealing a trans configuration and a specific dihedral angle. Molecules form 2D networks via hydrogen bonds, with pi-pi interactions observed between stacked benzene rings.

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Area of Science:

  • Crystallography
  • Molecular structure analysis
  • Supramolecular chemistry

Background:

  • Understanding molecular configurations is crucial for predicting material properties.
  • Hydrogen bonding and pi-pi interactions are key non-covalent forces driving self-assembly.
  • Naphthalene derivatives are widely studied for their electronic and optical properties.

Purpose of the Study:

  • To elucidate the crystal structure of the title molecule, C(12)H(9)NO(2).
  • To investigate the intermolecular interactions, including hydrogen bonding and pi-pi stacking.
  • To characterize the self-assembly behavior in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided geometric details.
  • Intermolecular interactions were identified and quantified using crystallographic data.

Main Results:

  • The molecule C(12)H(9)NO(2) was confirmed to have a trans configuration around the double bond.
  • A dihedral angle of 12.66(5)° was measured between the naphthalene and nitro-ethenyl groups.
  • Molecules self-assembled into a 2D network through C-H⋯O hydrogen bonds.
  • Evidence of pi-pi interactions was observed between stacked benzene rings with a centroid-centroid distance of 3.6337(11) Å.

Conclusions:

  • The crystal structure reveals specific molecular geometry and intermolecular interactions.
  • The observed hydrogen bonding and pi-pi stacking dictate the formation of 2D networks.
  • This structural information provides a basis for understanding the material properties of this naphthalene derivative.