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Related Concept Videos

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.
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: 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: 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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
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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2-Chloro-ethyl 4-nitro-benzoate.

Hao Wu1, Min-Hao Xie, Pei Zou

  • 1Key Laboratory of Nuclear Medicine, Ministry of Health, Jiangsu Key Laboratory of Molecular Nuclear Medicine, Jiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a novel compound, C(9)H(8)ClNO(4). Molecular analysis reveals specific dihedral angles and intermolecular interactions, including hydrogen bonds and short O⋯N contacts, influencing crystal packing.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

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 dictates intermolecular forces and overall stability.
  • Detailed crystallographic studies provide fundamental data for materials science and drug design.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(9)H(8)ClNO(4).
  • To analyze the molecular geometry, including the planarity of the carboxylate group relative to the benzene ring.
  • To identify and characterize intermolecular interactions, such as hydrogen bonds and short contacts, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of crystallographic data included bond length, bond angle, and dihedral angle calculations.
  • Intermolecular interactions were identified and quantified using geometric criteria.

Main Results:

  • The title compound, C(9)H(8)ClNO(4), crystallizes with two molecules in the asymmetric unit.
  • In each molecule, the carboxylate group is nearly coplanar with the benzene ring, with dihedral angles of 2.4(1)° and 4.9(1)°.
  • Weak C-H⋯O and C-H⋯Cl hydrogen bonds link molecules in the crystal, alongside a short O⋯N contact (2.7660(19) Å) between nitro groups of adjacent molecules.

Conclusions:

  • The crystal structure of C(9)H(8)ClNO(4) has been successfully determined.
  • The observed planarity and intermolecular interactions provide insights into the packing efficiency and stability of the crystal.
  • These findings contribute to the understanding of structure-property relationships in related organic compounds.