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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.
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.
Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
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...
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...

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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

N-(2,6-Dimethyl-phen-yl)-2-methyl-acetamide.

B Thimme Gowda, Sabine Foro, Hartmut Fuess

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

    The crystal structure of 2,6-dimethyl-N-(phenyl)acetamide (26DMPMA) reveals its relation to similar acetamide compounds. Molecules form chains via N-H⋯O hydrogen bonding in this novel crystal structure.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • The title compound, 2,6-dimethyl-N-(phenyl)acetamide (26DMPMA), shares structural similarities with related acetamide derivatives.
    • Understanding the precise structural features and intermolecular interactions of 26DMPMA is crucial for its potential applications.

    Purpose of the Study:

    • To elucidate the crystal structure of 2,6-dimethyl-N-(phenyl)acetamide (26DMPMA).
    • To compare the structural parameters of 26DMPMA with related acetamide compounds.
    • To identify and characterize the intermolecular interactions within the crystal lattice of 26DMPMA.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure of 26DMPMA.
    • Comparative analysis of bond lengths and angles was performed against related acetamide structures.

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    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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    09:45

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    Main Results:

    • The crystal structure of 26DMPMA (C(11)H(15)NO) was successfully determined.
    • Slight variations in bond parameters were observed when compared to N-(2,6-dimethyl-phen-yl)acetamide, N-(2,6-dimethyl-phen-yl)-2,2,2-trimethyl-acetamide, and 2-chloro-N-(2,6-dimethyl-phen-yl)acetamide.
    • The molecules of 26DMPMA are organized into chains through intermolecular N-H⋯O hydrogen bonding.

    Conclusions:

    • The crystal structure of 26DMPMA is closely related to other substituted acetamides, with distinct bond parameters.
    • Intermolecular N-H⋯O hydrogen bonding plays a significant role in the crystal packing of 26DMPMA, leading to chain formation.