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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
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...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Crystal structures and the Hirshfeld surface analysis of <i>(E)</i>-4-nitro-<i>N</i>'-(<i>o</i>-chloro, <i>o</i>- and <i>p</i>-methyl-benzyl-idene)benzene-sulfono-hydrazides.

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Crystal structure and Hirshfeld surface analysis of two (<i>E</i>)-<i>N</i>'-(<i>para</i>-substituted benzyl-idene) 4-chloro-benzene-sulfono-hydrazides.

Acta crystallographica. Section E, Crystallographic communications·2018
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Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-<i>N</i>'-[4-(piperidin-1-yl)benzyl-idene]aryl-sulfono-hydrazides.

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Crystal structure and Hirshfeld surface analysis of (<i>Z</i>)-4-chloro-<i>N</i>'-(4-oxo-thia-zol-idin-2-yl-idene)benzene-sulfono-hydrazide monohydrate.

Acta crystallographica. Section E, Crystallographic communications·2018
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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.

Acta crystallographica. Section E, Crystallographic communications·2018

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

2-Bromo-N-(2-chloro-phen-yl)acetamide.

B Thimme Gowda, Sabine Foro, P A Suchetan

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

    This study details the N-H bond conformation in a novel compound, revealing specific molecular arrangements and hydrogen bonding patterns in its crystal structure for chemical analysis.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Understanding molecular conformation is crucial in organic chemistry.
    • The specific arrangement of atoms influences a molecule's properties and reactivity.
    • Previous studies on similar chloroacetanilides provide a basis for comparison.

    Purpose of the Study:

    • To elucidate the precise three-dimensional structure of the title compound, C(8)H(7)BrClNO.
    • To analyze the conformation of the N-H bond relative to substituents.
    • To investigate intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond orientations (syn/anti) and hydrogen bonding networks.

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    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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  • Examination of weak intermolecular interactions, including halogen bonding.

    • Main Results:

    • The N-H bond was found to be syn to the 2-chloro substituent and anti to the C=O and C-Br bonds.
    • Molecules form chains along the a axis via N-H⋯O hydrogen bonds.
    • Weaker C-H⋯Cl and Br⋯Br interactions link these chains into columns.

    Conclusions:

    • The determined conformation is similar to related chloroacetanilides, suggesting a conserved structural motif.
    • Hydrogen bonding and weaker interactions dictate the crystal packing and solid-state architecture.
    • The findings contribute to the understanding of structure-property relationships in halogenated anilides.