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Related Concept Videos

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

2° Amines to N-Nitrosamines: Reaction with NaNO2

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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.
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

7.1K
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.
7.1K
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

10.3K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
10.3K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

4.4K
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...
4.4K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

1.9K
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...
1.9K
Rate-Determining Steps03:08

Rate-Determining Steps

30.3K
Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Bis(2-nitro-phen-yl)methane.

Daron E Janzen1, Laura E Crepeau1, Benjamin D Hageseth1

  • 1Department of Chemistry and Biochemistry, St Catherine University, 2004 Randolph Avenue, St Paul, MN 55105, USA.

Acta Crystallographica. Section E, Structure Reports Online
|September 25, 2014
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of C13H10N2O4, revealing significant twists in nitro groups and near-perpendicular benzene rings. Weak intermolecular interactions and pi-pi stacking influence crystal packing and molecular conformation.

Keywords:
crystal structure

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding molecular conformation and intermolecular forces is crucial for predicting material properties.
  • Nitroaromatic compounds exhibit diverse structural motifs and intermolecular interactions.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of the title compound, C13H10N2O4.
  • To analyze the conformational preferences of nitro groups and benzene rings within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
  • Analysis of dihedral angles and interatomic distances provided insights into molecular geometry and interactions.

Main Results:

  • The nitro groups displayed significant twists relative to the benzene rings (dihedral angles of 16.64° and 28.02°).
  • The benzene rings were found to be nearly perpendicular to each other (dihedral angle of 87.72°).
  • Short intermolecular contacts (N⋯O, C⋯O, and π-π interactions) were identified, suggesting weak attractive forces influencing crystal packing.

Conclusions:

  • The crystal structure of C13H10N2O4 is characterized by strained conformations and significant intermolecular interactions.
  • These findings contribute to the understanding of structure-property relationships in nitroaromatic systems.