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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.
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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4-Nitro-benzyl 2-chloro-acetate.

Kai Zhu1, Yan-Hua Wang, Hui Liu

  • 1College of Biotechnology and Pharmaceutical Engineering, 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

The crystal structure of C(9)H(8)ClNO(4) reveals a nearly planar acetate group attached to an aromatic ring. Intermolecular interactions, including C-H⋯O bonds and π-π stacking, contribute to a stable molecular network.

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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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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Area of Science:

  • Crystallography
  • Molecular structure analysis
  • Organic chemistry

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Crystal structure analysis provides detailed insights into molecular geometry and intermolecular forces.

Purpose of the Study:

  • To determine and describe the crystal structure of the title compound, C(9)H(8)ClNO(4).
  • To investigate the molecular conformation and intermolecular interactions present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the crystal structure.
  • Analysis of bond lengths, bond angles, dihedral angles, and intermolecular contacts (C-H⋯O and π-π interactions) was performed.

Main Results:

  • The acetate moiety exhibits near planarity with a maximum deviation of 0.015(3) Å.
  • The acetate group is oriented at a dihedral angle of 73.03(3)° relative to the aromatic ring plane.
  • Intermolecular C-H⋯O interactions and π-π contacts (centroid-centroid distance of 4.000(1) Å) were identified, forming a stable network.

Conclusions:

  • The crystal structure of C(9)H(8)ClNO(4) is characterized by specific molecular geometry and significant intermolecular interactions.
  • These interactions, including hydrogen bonding and π-π stacking, play a key role in stabilizing the overall crystal structure.