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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.
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...
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: 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...
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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Ethyl 4-chloro-3,5-dinitro-benzoate.

Hao Wu1, Min-Hao Xie, Ya-Ling Liu

  • 1Jiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a chlorinated nitroaromatic compound. Analysis reveals specific dihedral angles and intermolecular interactions, including hydrogen bonding and pi-pi stacking, crucial for understanding its solid-state properties.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Solid-State Chemistry

Background:

  • Understanding the solid-state structure of organic compounds is essential for predicting their physical and chemical properties.
  • Nitroaromatic compounds are widely used in various industrial applications, making their structural characterization important.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(9)H(7)ClN(2)O(6).
  • To investigate the intermolecular interactions governing the compound's solid-state packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of dihedral angles between functional groups and the benzene ring.

Main Results:

  • The nitro groups and ester group exhibit distinct dihedral angles (44.0(1)°, 89.6(1)°, and 164.1(1)°) with the benzene ring.
  • Molecules are interconnected by weak C-H⋯O hydrogen bonds.
  • Significant π-π stacking interactions were observed between molecules, with a centroid-centroid distance of 3.671(2) Å.

Conclusions:

  • The crystal structure is stabilized by a combination of hydrogen bonding and π-π stacking.
  • The observed dihedral angles provide insight into the electronic and steric influences of the substituents on the aromatic ring.