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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...
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...
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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2,4,6-Trinitro-phenyl 4-methyl-benzoate.

Rodolfo Moreno-Fuquen1, Fabricio Mosquera, Javier Ellena

  • 1Departamento de Química - Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia.

Acta Crystallographica. Section E, Structure Reports Online
|January 4, 2013
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of a novel compound, C(14)H(9)N(3)O(8). Researchers observed specific dihedral angles between benzene rings and ester group rotations, revealing unique crystal packing through C-H⋯O interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Crystal engineering utilizes intermolecular forces to design materials with desired characteristics.

Purpose of the Study:

  • To elucidate the precise molecular geometry and crystal packing of the title compound, C(14)H(9)N(3)O(8).
  • To investigate the role of intermolecular interactions in the supramolecular assembly of this organic molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and molecular conformation.
  • Analysis of intermolecular contacts, specifically C-H⋯O interactions, was performed to understand crystal packing.

Main Results:

  • The benzene rings within the molecule exhibit a significant dihedral angle of 69.02(5)°.
  • A notable rotation of 25.86(9)° was observed for the central ester group relative to the p-tolyl group.
  • Molecules self-assemble into helical chains along the [010] direction via C-H⋯O hydrogen bonding.

Conclusions:

  • The determined molecular structure and dihedral angles provide fundamental insights into the conformational preferences of this compound.
  • The observed helical chain formation highlights the importance of C-H⋯O interactions in directing crystal structure and supramolecular organization.