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Related Concept Videos

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.
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.
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.
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.
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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4-Formyl-2-nitro-phenyl 4-bromo-benzoate.

Rodolfo Moreno-Fuquen1, Geraldine Hernandez, Javier Ellena

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

Acta Crystallographica. Section E, Structure Reports Online
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PubMed
Summary

This study details the molecular structure of C14H8BrNO5, revealing specific dihedral angles between benzene rings and functional groups. Molecular interactions in the crystal structure were also analyzed.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Crystallographic studies provide detailed insights into molecular conformations and intermolecular interactions in the solid state.

Purpose of the Study:

  • To elucidate the detailed molecular structure of the title compound, C14H8BrNO5.
  • To investigate the conformational preferences of the substituted benzene rings and the ester group.
  • To characterize the intermolecular interactions and crystal packing in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Geometric parameters, including bond lengths, bond angles, and dihedral angles, were analyzed.
  • Intermolecular interactions, such as hydrogen bonds and halogen bonds, were identified and quantified.

Main Results:

  • The crystal structure of C14H8BrNO5 was determined, revealing a dihedral angle of 62.90(7)° between the benzene rings.
  • The ester group exhibited significant twisting relative to the substituted benzene rings (71.67(7)° and 8.78(15)°).
  • Weak C-H⋯O interactions formed C(12) chains, and Br⋯Br halogen interactions [3.523(3) Å] were observed, stabilizing the crystal structure.

Conclusions:

  • The study provides a comprehensive structural characterization of C14H8BrNO5 at the molecular and crystalline level.
  • The observed conformational features and intermolecular interactions offer insights into the packing forces governing the solid-state structure.
  • This detailed structural information can serve as a basis for further studies on the compound's physical and chemical properties.