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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...
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.
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.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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.

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Related Experiment Video

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

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1-(2,6-Dichloro-phen-yl)indolin-2-one.

Muhammad Hanif, Muhammad Rafiq, Muhammad Saleem

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a dichlorinated indole derivative. The molecule features a planar indole ring system and a phenyl ring connected by a specific dihedral angle, with intermolecular hydrogen bonds stabilizing the crystal structure.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Indole derivatives are important scaffolds in medicinal chemistry and materials science.
    • Understanding the solid-state structure of novel organic compounds is crucial for predicting their properties and reactivity.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(14)H(9)Cl(2)NO.
    • To analyze the molecular geometry, including the orientation of the indole and phenyl rings.
    • To identify and characterize intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
    • Intermolecular interactions, such as hydrogen bonds and C-H···π interactions, were identified and analyzed.

    Main Results:

    • The title compound, C(14)H(9)Cl(2)NO, was successfully crystallized and its structure determined.
    • The indole ring system was found to be planar, with a maximum deviation of 0.020(2) Å for the nitrogen atom.
    • A dihedral angle of 72.17(3)° was observed between the indole and phenyl ring systems.
    • Weak intermolecular C-H⋯O hydrogen bonds and C-H⋯π interactions were identified as stabilizing forces in the crystal structure.

    Conclusions:

    • The crystal structure of the title compound reveals a specific spatial arrangement of its aromatic systems.
    • The identified intermolecular interactions play a significant role in the molecular packing and stability of the compound in the solid state.
    • This structural information provides a foundation for further investigations into the compound's chemical and physical properties.