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Related Concept Videos

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.
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: 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.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Published on: January 19, 2016

Methyl 4-nitro-benzoate.

Hao Wu1, Min-Hao Xie, Pei Zou

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

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of a nitrobenzoic acid derivative, revealing specific spatial arrangements of its nitro and methoxy-carbonyl groups relative to the benzene ring. Crystal analysis identified weak intermolecular hydrogen bonds contributing to its solid-state structure.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the precise spatial arrangement of functional groups in organic molecules is crucial for predicting their chemical behavior and physical properties.
  • Nitrobenzoic acid derivatives are important intermediates in various chemical syntheses.

Purpose of the Study:

  • To elucidate the detailed molecular geometry of the title compound, C(8)H(7)NO(4).
  • To investigate the intermolecular interactions present in the crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided geometric insights.
  • Identification of intermolecular hydrogen bonds through crystallographic analysis.

Main Results:

  • The nitro group is nearly coplanar with the benzene ring (dihedral angle = 0.6°).
  • The methoxy-carbonyl group exhibits a dihedral angle of 8.8° relative to the benzene ring.
  • Weak intermolecular aromatic C-H⋯O(carboxyl) and C-H⋯O(nitro) hydrogen bonds were observed in the crystal lattice.

Conclusions:

  • The study provides precise crystallographic data on the molecular conformation of the title compound.
  • The identified hydrogen bonding network offers insights into the crystal packing and stability of this nitrobenzoic acid derivative.