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Related Concept Videos

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:
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...
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes


The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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.
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...
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...

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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

2-(4-Amino-pyridinio)acetate.

Ge Liu1

  • 1Chifeng University, Chifeng 024000, People's Republic of China.

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

This study details the crystal structure of a pyridinium compound, highlighting a significant dihedral angle and a layered network formed by intermolecular hydrogen bonds. These findings contribute to understanding molecular interactions in organic crystals.

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the three-dimensional arrangement of atoms in organic compounds is crucial for predicting their properties.
  • Hydrogen bonding plays a significant role in the self-assembly and structural organization of molecules.
  • Detailed structural analysis provides insights into intermolecular forces and crystal packing.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(7)H(8)N(2)O(2).
  • To quantify the dihedral angle between the pyridinium ring and the carboxyl-atomethyl group.
  • To identify and characterize the intermolecular interactions, including hydrogen bonding, present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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Direct Detection of the Acetate-forming Activity of the Enzyme Acetate Kinase
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Direct Detection of the Acetate-forming Activity of the Enzyme Acetate Kinase

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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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Direct Detection of the Acetate-forming Activity of the Enzyme Acetate Kinase
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Direct Detection of the Acetate-forming Activity of the Enzyme Acetate Kinase

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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
06:00

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

  • Analysis of bond lengths, bond angles, and torsion angles provided detailed geometric information.
  • Intermolecular interactions, such as hydrogen bonds, were identified using geometric criteria.

    • Main Results:

    • The crystal structure of C(7)H(8)N(2)O(2) was successfully determined.
    • A notable dihedral angle of 74.5(1)° was observed between the pyridinium ring and the carboxyl-atomethyl group.
    • A robust, layered hydrogen-bonded network was formed by intermolecular N-H⋯O interactions, oriented perpendicular to the [010] direction.
    • Weak C-H⋯O hydrogen bonds were also identified within the structure.

    Conclusions:

    • The crystal structure reveals specific geometric preferences and conformational arrangements in the title compound.
    • The identified hydrogen-bonded network significantly influences the overall crystal packing and stability.
    • The findings contribute to the understanding of structure-property relationships in organic crystalline materials.