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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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Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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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...
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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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Structure and Nomenclature of Alcohols and Phenols02:23

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Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and...
17.0K
Reactions at the Benzylic Position: Oxidation and Reduction00:59

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4.3K
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.
4.3K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

8.3K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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3,4-Di-methyl-phenyl benzoate.

Rodolfo Moreno-Fuquen1, Mauricio Rendón1, Alan R Kennedy2

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

Acta Crystallographica. Section E, Structure Reports Online
|April 26, 2014
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Summary
This summary is machine-generated.

This study details the molecular structure of a C15H14O2 compound, revealing specific dihedral angles between its terminal rings and ester group. Molecular packing in the crystal is influenced by weak hydrogen bonds forming chains.

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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 properties and reactivity.
  • Crystal structure analysis provides precise details on molecular conformation and intermolecular interactions.
  • Esters are a fundamental class of organic compounds with diverse applications.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C15H14O2.
  • To quantify the dihedral angles between the aromatic rings and the central ester group.
  • To identify and describe the intermolecular interactions governing crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • The crystal structure was solved and refined to high accuracy.
  • Intermolecular interactions, specifically C-H⋯O hydrogen bonds, were analyzed.

Main Results:

  • The terminal rings exhibit a dihedral angle of 52.39(4)°.
  • The central ester group is twisted relative to the benzene and phenyl rings by 60.10(4)° and 8.67(9)°, respectively.
  • Molecules are arranged in C(6) chains along the [100] direction, facilitated by weak C-H⋯O hydrogen bonds.

Conclusions:

  • The study provides precise structural data for the C15H14O2 compound.
  • The observed molecular conformation is influenced by steric and electronic factors.
  • The identified hydrogen bonding network dictates the crystal packing and supramolecular architecture.