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Related Concept Videos

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.
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.
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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: 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.
Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.

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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-(Carbazol-9-yl)acetic acid.

Min-Hao Xie1, Pei Zou, Yong-Jun He

  • 1Jiangsu Institute of Nuclear Medicine, Wuxi 214063, 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 C(14)H(11)NO(2) compound, revealing a nearly planar tricyclic aromatic system. Hydrogen bonds play a role in stabilizing the crystal structure.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding the three-dimensional structure of organic compounds is crucial for predicting their properties and reactivity.
  • Tricyclic aromatic systems are prevalent in pharmaceuticals and advanced materials, necessitating detailed structural analysis.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C(14)H(11)NO(2).
  • To analyze the planarity of the tricyclic aromatic system and the orientation of the carboxyl group.
  • To investigate potential intermolecular interactions contributing to crystal stabilization.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Geometric parameters, including bond lengths, bond angles, and dihedral angles, were precisely measured.
  • Intermolecular interactions, such as hydrogen bonding, were identified and analyzed.

Main Results:

  • The tricyclic aromatic ring system of C(14)H(11)NO(2) exhibits near-planarity, with a maximum deviation of 0.025 Å.
  • A small dihedral angle of 2.8(5)° was observed between the two benzene rings.
  • The carboxyl group is oriented nearly perpendicular to the pyrrole ring, with a dihedral angle of 88.5(1)°.

Conclusions:

  • The C(14)H(11)NO(2) compound possesses a highly defined and nearly planar tricyclic aromatic core.
  • Intermolecular O-H⋯O hydrogen bonds are likely significant in stabilizing the observed crystal packing.
  • The precise structural data provides a foundation for further studies on the compound's physical and chemical properties.