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Related Concept Videos

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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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.
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...
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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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 5, 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

2,2-Dichloro-N-(2,5-dichloro-phen-yl)acetamide.

B Thimme Gowda, Sabine Foro, Hartmut Fuess

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    The N-H bond conformation in C(8)H(5)Cl(4)NO is syn to one chloro group and anti to another. Molecular chains form via N-H⋯O hydrogen bonding in the crystal structure.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Acetanilides are a class of organic compounds with diverse applications.
    • Understanding the conformational preferences of substituents is crucial for predicting chemical behavior.
    • Hydrogen bonding plays a significant role in crystal packing and material properties.

    Purpose of the Study:

    • To determine the specific conformation of the N-H bond in the title compound, C(8)H(5)Cl(4)NO.
    • To compare the bond parameters with related acetanilide structures.
    • To elucidate the intermolecular interactions present in the crystal lattice.

    Main Methods:

    • X-ray crystallography was employed to analyze the crystal structure of C(8)H(5)Cl(4)NO.
    • Analysis of bond parameters and intermolecular distances.

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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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  • Identification of hydrogen bonding networks.

    • Main Results:

    • The N-H bond in C(8)H(5)Cl(4)NO adopts a syn conformation relative to the 2-chloro substituent and an anti conformation relative to the 5-chloro substituent.
    • The determined bond parameters are comparable to those observed in 2,2-dichloro-N-phenyl-acetamide and other acetanilides.
    • The crystal structure reveals that molecules are organized into chains facilitated by N-H⋯O hydrogen bonding.

    Conclusions:

    • The study precisely defines the N-H bond conformation in the tetrachlorinated acetanilide derivative.
    • The findings provide insights into the structure-property relationships of substituted acetanilides.
    • The identified hydrogen bonding pattern contributes to the understanding of crystal engineering principles for this class of compounds.