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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...
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.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Published on: November 15, 2017

N'-(2,4-Dinitro-phen-yl)benzohydrazide.

Aamer Saeed, Ifzan Arshad, Ulrich Flörke

    Acta Crystallographica. Section E, Structure Reports Online
    |August 21, 2012
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a novel organic compound, C(13)H(10)N(4)O(5). It reveals specific molecular orientations and hydrogen bonding that lead to zigzag chain formation in the crystal lattice.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding molecular packing and intermolecular interactions is crucial for predicting material properties.
    • Crystal structure analysis provides fundamental insights into the solid-state behavior of organic compounds.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(13)H(10)N(4)O(5).
    • To investigate the molecular geometry, including dihedral and torsion angles.
    • To characterize the hydrogen bonding network and its influence on crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of bond lengths, bond angles, and torsion angles provided geometric details.
    • Identification and analysis of intermolecular interactions, specifically N-H⋯O hydrogen bonds, were performed.

    Main Results:

    • The crystal structure of C(13)H(10)N(4)O(5) was determined.
    • A near-perpendicular orientation between aromatic ring planes (dihedral angle = 75.94°) and a significant C-N-N-C torsion angle (88.7°) were observed.
    • Nitro groups were found to be nearly coplanar with their attached rings, facilitating an intramolecular N-H⋯O hydrogen bond forming an S(6) ring.
    • Intermolecular N-H⋯O hydrogen bonds were identified, linking molecules into zigzag chains along the [100] direction.

    Conclusions:

    • The specific molecular conformation and intramolecular hydrogen bonding dictate the crystal packing.
    • The observed zigzag chain formation through intermolecular hydrogen bonds is a key feature of the crystal structure.
    • This structural characterization provides a foundation for understanding the physical and chemical properties of this compound.