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Related Concept Videos

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...
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.
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...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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4-[(E)-1-Naphthyl-diazen-yl]phenol.

Leonid A Aslanov1, Ksenia A Paseshnichenko, Alexandr V Yatsenko

  • 1Department of Chemistry, Moscow State University, 119992 Moscow, Russian Federation.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

The crystal structure of Solvent Yellow 8, a dye molecule, reveals two independent molecules with slightly distorted planarity. These molecules form polymeric chains through hydrogen bonding in the solid state.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Area of Science:

  • Crystallography
  • Materials Science
  • Organic Chemistry

Background:

  • Solvent Yellow 8 (C.I. 13900) is an azo dye with industrial applications.
  • Understanding the solid-state structure of dyes is crucial for predicting their properties and performance.

Purpose of the Study:

  • To elucidate the crystal structure of C.I. Solvent Yellow 8.
  • To investigate the molecular conformation and intermolecular interactions in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed.
  • The crystal structure was solved and refined.

Main Results:

  • The asymmetric unit contains two crystallographically independent molecules of C.I. Solvent Yellow 8 (C16H12N2O).
  • Both molecules exhibit slight deviations from planarity, with dihedral angles between the benzene and naphthalene systems ranging from 5.69° to 9.04°.
  • O-H⋯N hydrogen bonds link the independent molecules into a 1D polymeric chain along the [001] direction.

Conclusions:

  • The crystal packing of C.I. Solvent Yellow 8 is dominated by hydrogen bonding, forming extended polymeric chains.
  • The observed molecular distortions and hydrogen bonding patterns provide insights into the solid-state behavior of this azo dye.