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Related Concept Videos

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.
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

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).
Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
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: 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...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

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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Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-<i>N</i>'-benzyl-idene-4-chloro-benzene-sulfono-hydrazide and of its (<i>E</i>)-4-chloro-<i>N</i>'-(<i>ortho</i>- and <i>para</i>-methyl-benzyl-idene)benzene-sulfono-hydrazide derivatives.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

N-(2,3-Dimethyl-phen-yl)benzamide.

B Thimme Gowda, Miroslav Tokarčík, Jozef Kožíšek

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

    This study reveals the anti conformation of the N-H bond in a novel benzanilide derivative, differing from related chloro-substituted compounds. Molecular structure and hydrogen bonding in the crystalline state were elucidated.

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    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Benzanilides are a significant class of organic compounds with diverse applications.
    • Understanding the conformational preferences of substituents and functional groups is crucial for predicting molecular properties and reactivity.
    • Previous studies have established typical conformations in related benzanilide structures.

    Purpose of the Study:

    • To elucidate the molecular structure and conformation of a specific benzanilide derivative, C(15)H(15)NO.
    • To compare the observed N-H bond conformation with related structures containing different substituents.
    • To investigate intermolecular interactions and crystal packing in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Conformational analysis was performed based on the determined atomic coordinates.
    • Analysis of intermolecular interactions, including hydrogen bonding and close contacts, was conducted.

    Main Results:

    • The N-H bond adopts an anti conformation relative to ortho and meta-methyl groups on the aniline ring.
    • The amide group exhibits anti conformation between N-H and C=O bonds, consistent with other benzanilides.
    • A significant dihedral angle of 84.1° between the benzoyl and aniline rings and a twist of 23.0° for the amide group were observed.
    • Positional disorder of the aniline ring was identified with site occupancies of 0.80 and 0.20.
    • N-H⋯O hydrogen bonds form chains along the b axis, with an intramolecular C-H⋯O contact also present.

    Conclusions:

    • The study provides detailed structural and conformational insights into the title benzanilide compound.
    • The observed anti conformation of the N-H bond highlights the influence of methyl substituents on molecular geometry.
    • The crystal structure is stabilized by intermolecular hydrogen bonding, influencing the overall packing arrangement.