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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.
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...
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...
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...
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

2,5-Dimethyl-1,3-dinitro-benzene.

Dean H Johnston1, Heather M Crather

  • 1Department of Chemistry, Otterbein University, Westerville, OH 43081, USA.

Acta Crystallographica. Section E, Structure Reports Online
|November 8, 2011
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a nitrated p-xylene derivative, revealing antiparallel molecular stacking and C-H⋯O interactions that form puckered sheets. The compound exhibits methyl group disorder and non-merohedral twinning.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Nitration of aromatic compounds is a key synthetic route.
  • Understanding crystal packing influences material properties.
  • X-ray crystallography provides detailed molecular and structural information.

Purpose of the Study:

  • To elucidate the crystal structure of a novel nitrated p-xylene derivative.
  • To investigate intermolecular interactions and their role in crystal packing.
  • To characterize the twinning and disorder within the crystal.

Main Methods:

  • Single-crystal X-ray diffraction was employed for structural determination.
  • The crystal structure was refined, including analysis of molecular conformation and symmetry.
  • Non-merohedral twinning was identified and modeled.

Main Results:

  • The compound, C(8)H(8)N(2)O(4), was synthesized via p-xylene nitration.
  • Molecules exhibit antiparallel stacking along the c axis with specific nitro group rotations.
  • C-H⋯O interactions lead to puckered sheets, and methyl group disorder was observed.

Conclusions:

  • The crystal structure reveals unique packing motifs driven by intermolecular forces.
  • The presence of disorder and twinning provides insights into crystal growth and formation.
  • This structural data contributes to the understanding of nitroaromatic compounds.