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Related Concept Videos

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.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

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 the...
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.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

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 constants depend...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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2-Methyl-3-nitro-benzonitrile.

Guo-Zhi Han1, Lu-Na Han, Ran-Zhe Lu

  • 1College of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, 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 C(8)H(6)N(2)O(2), revealing two independent molecules with specific dihedral angles. Intramolecular and intermolecular hydrogen bonds, along with pi-pi contacts, dictate the compound's crystal packing and molecular conformation.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
  • The specific arrangement of molecules in a crystal lattice influences intermolecular interactions and overall material behavior.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(8)H(6)N(2)O(2).
  • To investigate the types and significance of intermolecular and intramolecular interactions within the crystal lattice.
  • To characterize the conformational preferences of the independent molecules.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
  • The asymmetric unit was analyzed, revealing the presence of two independent molecules.
  • Geometric parameters, including dihedral angles and hydrogen bond distances, were precisely measured.

Main Results:

  • The asymmetric unit contains two independent C(8)H(6)N(2)O(2) molecules with a dihedral angle of 1.68° between their aromatic rings.
  • Intramolecular C-H⋯O hydrogen bonds form two non-planar six-membered rings with envelope and twisted conformations.
  • Intermolecular C-H⋯O hydrogen bonds facilitate molecular linkage, and π-π contacts between benzene rings were observed with distances of 3.752(3) and 3.874(3) Å.

Conclusions:

  • The crystal structure is stabilized by a combination of intramolecular and intermolecular hydrogen bonding and π-π stacking interactions.
  • The observed conformations and intermolecular contacts provide insights into the packing efficiency and potential properties of the compound.
  • This detailed structural analysis contributes to the understanding of structure-property relationships in organic crystalline materials.