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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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.
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).
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...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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.

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Related Experiment Video

Updated: Jun 5, 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

N-Phenylpyridine-2-carb-amide.

Yu-Guo Zhuang1, Hua-Jiang Jiang, Zhi Hong

  • 1School of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of a novel organic compound, C(12)H(10)N(2)O. Researchers identified a near-planar configuration and an intramolecular hydrogen bond, crucial for understanding its chemical properties.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is fundamental.
  • Intramolecular hydrogen bonds play a significant role in stabilizing molecular conformations and influencing chemical reactivity.

Purpose of the Study:

  • To elucidate the precise molecular geometry of the title compound, C(12)H(10)N(2)O.
  • To investigate the presence and characteristics of intramolecular hydrogen bonding within the molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
  • Analysis of the crystal structure revealed the dihedral angle between the aromatic rings and the hydrogen bonding network.

Main Results:

  • The dihedral angle between the pyridine and phenyl rings was found to be 1.8(1)°, indicating a nearly planar arrangement.
  • An intramolecular N-H⋯N hydrogen bond was identified between the pyridine nitrogen and the amide nitrogen.

Conclusions:

  • The title compound C(12)H(10)N(2)O exhibits a specific, near-planar conformation due to the observed dihedral angle.
  • The identified intramolecular hydrogen bond is a key structural feature, likely influencing the molecule's stability and interactions.