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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.
IUPAC Nomenclature of Carboxylic Acids01:16

IUPAC Nomenclature of Carboxylic Acids

IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
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...
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:
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.

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

Published on: November 23, 2016

N,N'-Bis(2-hydroxy-ethyl)benzene-1,4-dicarboxamide.

Gabriela Bednarek, Joachim Kusz, Alicja Ratuszna

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

    This study details the crystal structure of a novel organic compound, C(12)H(16)N(2)O(4). The molecule exhibits a unique centrosymmetric structure with specific amide group twisting and forms a 3D framework via hydrogen bonding.

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    Published on: December 4, 2016

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding molecular structure and intermolecular interactions is crucial for designing new materials.
    • Crystal engineering relies on predicting and controlling how molecules assemble in the solid state.

    Purpose of the Study:

    • To elucidate the crystal structure and hydrogen bonding network of the title compound, C(12)H(16)N(2)O(4).
    • To analyze the specific molecular conformation, including amide group orientation and its impact on crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of intermolecular interactions, specifically hydrogen bonds (N-H⋯O and O-H⋯O), was performed.

    Main Results:

    • The title compound, C(12)H(16)N(2)O(4), crystallizes in a centrosymmetric manner.
    • A significant twist (14.40°) of the amide group relative to the benzene ring was observed.
    • Molecules self-assemble into a three-dimensional framework through a combination of N-H⋯O and O-H⋯O=C hydrogen bonds.

    Conclusions:

    • The determined crystal structure provides fundamental insights into the solid-state behavior of this organic molecule.
    • The observed hydrogen bonding patterns are key to the formation of the 3D framework, influencing material properties.