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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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.

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Role of Reduced Coenzymes NADH and FADH₂

Role of Reduced Coenzymes NADH and FADH₂

The energy released from the breakdown of the chemical bonds within nutrients can be stored either through the reduction of electron carriers or in the bonds of adenosine triphosphate (ATP). In living systems, a small class of compounds functions as mobile electron carriers, molecules that bind to and shuttle high-energy electrons between compounds in pathways. The principal electron carriers that will be considered originate from the B vitamin group and are derivatives of nucleotides; they are...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

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Updated: May 30, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

(E)-N'-[(2-Hydroxynaphthalen-1-yl)methylidene]nicotinohydrazide.

Shi-Yong Liu, Qin-Qin Guo, Yu-Mei Hao

Acta Crystallographica. Section E, Structure Reports Online

|August 13, 2011

Summary

This study details the molecular structure of C(17)H(13)N(3)O(2), revealing a near-planar conformation stabilized by intramolecular hydrogen bonding. Intermolecular hydrogen bonds further organize these molecules into crystal chains.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
Hydrogen bonding plays a significant role in dictating crystal packing and material properties.

Purpose of the Study:

To elucidate the crystal structure and intermolecular interactions of the title compound, C(17)H(13)N(3)O(2).
To analyze the conformational preferences and hydrogen bonding patterns within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
Analysis of hydrogen bonding networks, including intramolecular and intermolecular interactions, was performed.

Main Results:

The molecule exhibits a dihedral angle of 12.2° between the naphthyl and pyridine rings, indicating a near-planar conformation.
An intramolecular O-H⋯N hydrogen bond forms a six-membered ring (S(6) motif), contributing to the molecule's planarity.
Intermolecular N-H⋯N hydrogen bonds link molecules into chains along the crystallographic a axis.

Conclusions:

The crystal structure of C(17)H(13)N(3)O(2) is characterized by significant planarity due to intramolecular hydrogen bonding.
The observed intermolecular hydrogen bonding dictates the formation of one-dimensional chains in the solid state.