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Related Concept Videos

Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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 eliminated to generate the benzyne...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

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 phenols...
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...

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2-(1H-Benzimidazol-2-yl)-4,6-dichloro-phenol.

Li-Lu Han1

  • 1Hunan Yongzhou Vocational College, Yongzhou Hunan 425100, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel compound, C(13)H(8)Cl(2)N(2)O, revealing its planar structure and intricate intermolecular hydrogen bonding. This study details the crystal packing and interactions of this dichloro-hydroxy-benzaldehyde derivative.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • The synthesis and structural characterization of novel organic compounds are fundamental to advancing chemical science.
  • Understanding intermolecular interactions, such as hydrogen bonding and pi-pi stacking, is crucial for predicting material properties and designing new molecular architectures.

Purpose of the Study:

  • To synthesize and characterize a new compound derived from 3,5-dichloro-2-hydroxy-benzaldehyde and 1,2-diaminobenzene.
  • To elucidate the molecular and crystal structure of the synthesized compound, focusing on its planarity and hydrogen bonding network.
  • To investigate the role of pi-pi interactions in the crystal packing of the title molecule.

Main Methods:

  • Chemical synthesis involving the reaction of 3,5-dichloro-2-hydroxy-benzaldehyde with 1,2-diaminobenzene in methanol.
  • Single-crystal X-ray diffraction to determine the molecular geometry, planarity, and crystal structure.
  • Analysis of intra- and intermolecular hydrogen bonds and pi-pi interactions.

Main Results:

  • Successful synthesis of the target compound C(13)H(8)Cl(2)N(2)O.
  • The molecule exhibits near-planarity with a mean deviation of 0.037(2) Å from the plane.
  • An intramolecular O-H⋯N hydrogen bond was identified within the molecule.
  • In the crystal lattice, N-H⋯O hydrogen bonds link molecules into polymeric chains along the [001] direction.
  • Pi-pi interactions between the dichloro-phenol and benzoimidazole rings stabilize the crystal structure with centroid-centroid distances of 3.535(2) and 3.724(2) Å.

Conclusions:

  • The study successfully synthesized and characterized a novel organic compound.
  • The compound's crystal structure is stabilized by a combination of intra- and intermolecular hydrogen bonding and pi-pi stacking interactions.
  • The findings provide insights into the structure-property relationships of related heterocyclic compounds.