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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.
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: 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...
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...
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...

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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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1-Chloro-2-methyl-3-nitro-benzene.

Matthew A Pearce1, Joseph M Tanski

  • 1Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.

Acta Crystallographica. Section E, Structure Reports Online
|April 28, 2011
PubMed
Summary

This study details the crystal structure of a specific chlorinated methyl nitrobenzene compound. The nitro group exhibits a significant twist relative to the benzene ring, indicating unique molecular geometry.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the spatial arrangement of substituents on aromatic rings is crucial in organic chemistry.
  • Previous studies have explored various substituted benzene derivatives, but specific conformational details of chloro, methyl, and nitro groups in proximity require further investigation.

Purpose of the Study:

  • To elucidate the precise three-dimensional structure of the title compound, C(7)H(6)ClNO(2).
  • To quantify the degree of non-planarity of the nitro group with respect to the benzene ring.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
  • The crystallographic data was processed to obtain precise atomic coordinates and bond parameters.

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Main Results:

  • The crystal structure of C(7)H(6)ClNO(2) was successfully determined.
  • The chloro, methyl, and nitro groups were found to be adjacent on the benzene ring in a specific sequence.
  • A significant dihedral angle of 38.81(5)° was observed between the mean plane of the nitro group and the benzene ring.

Conclusions:

  • The study provides definitive structural data for this substituted benzene derivative.
  • The observed twist of the nitro group suggests steric hindrance or electronic effects influencing the molecule's conformation.
  • This detailed structural information can aid in predicting the reactivity and properties of related compounds.