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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:
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
IR and UV–Vis Spectroscopy of Carboxylic Acids01:28

IR and UV–Vis Spectroscopy of Carboxylic Acids

In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency, 1710 cm−1. The C=O bond of the...
Spectroscopy of Carboxylic Acid Derivatives01:26

Spectroscopy of Carboxylic Acid Derivatives

Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and unsymmetrical carbonyl vibration.
In the...
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.

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Related Experiment Video

Updated: Jun 1, 2026

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
05:07

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

Published on: June 23, 2019

1H-Pyrrole-2-carboxylic acid.

Gui Hong Tang1, Dong Dong Li, Gang Huang

  • 1Department of Chemistry, Jinan University, Guangzhou, Guangdong 510632, People's Republic of China.

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

The crystal structure of C(5)H(5)NO(2) reveals a nearly planar pyrrole ring and carboxyl group. Molecules form dimers via hydrogen bonds, which further assemble into chains along the crystal

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Last Updated: Jun 1, 2026

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Published on: June 23, 2019

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Published on: June 10, 2021

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the molecular arrangement and intermolecular interactions in organic compounds is crucial for predicting their physical and chemical properties.
  • Pyrrole derivatives with carboxyl substituents are important in various chemical and biological applications.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(5)H(5)NO(2).
  • To investigate the intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
  • To determine the planarity of the pyrrole ring and its carboxyl substituent.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
  • Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
  • Intermolecular interactions, including hydrogen bonds, were identified and characterized.

Main Results:

  • The pyrrole ring and the carboxyl substituent were found to be nearly coplanar, with a small dihedral angle of 11.7(3)°.
  • Adjacent molecules form inversion dimers through pairs of O-H⋯O hydrogen bonds.
  • These dimers are further connected by N-H⋯O hydrogen bonds, leading to the formation of extended chains along the crystallographic a axis.

Conclusions:

  • The crystal packing of C(5)H(5)NO(2) is dominated by a network of hydrogen bonds, forming dimers and chains.
  • The near-coplanarity of the pyrrole ring and carboxyl group influences the overall molecular conformation and crystal packing.
  • This structural information provides a foundation for understanding the compound's reactivity and potential applications.