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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

10.3K
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...
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Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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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.
7.4K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

3.6K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
3.6K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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.
6.5K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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9.2K
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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4-Formyl-2-nitro-phenyl 2-chloro-benzoate.

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This study details the crystal structure of a novel chloro-nitro-ester compound. Molecular analysis reveals specific dihedral angles between aromatic rings and the central ester group, with C-H⋯O bonds facilitating chain formation in the crystal lattice.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their chemical and physical properties.
  • The presence of chloro and nitro substituents on aromatic rings can significantly influence molecular conformation and intermolecular interactions.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C14H8ClNO5.
  • To quantify the dihedral angles between the aromatic rings and the central ester group.
  • To investigate the intermolecular interactions, specifically hydrogen bonding, that govern crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles was performed.
  • Identification and characterization of intermolecular interactions, including hydrogen bonds, were conducted.

Main Results:

  • The dihedral angle between the two benzene rings in the title compound was determined to be 19.55(9)°.
  • The ester group exhibited significant dihedral angles of 53.28(13)° and 36.93(16)° with the nitro- and chloro-substituted rings, respectively.
  • The nitro group displayed a dihedral angle of 19.24(19)° with its attached benzene ring. Molecules are linked via C-H⋯O hydrogen bonds, forming C(7) chains along the [100] direction.

Conclusions:

  • The crystal structure of C14H8ClNO5 reveals a non-planar conformation due to the specific dihedral angles between its constituent parts.
  • Weak intermolecular C-H⋯O hydrogen bonds play a significant role in organizing the molecules into extended chain structures within the crystal.
  • These structural insights are fundamental for understanding the solid-state properties and potential applications of this class of compounds.