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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.

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Related Experiment Video

Updated: Jun 1, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Published on: January 21, 2020

N'-(2-Methoxy-benzyl-idene)nicotinohydrazide.

Ping Wang¹, Cong Li, Yong-Qing Su

¹Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

Researchers synthesized a novel compound, C(14)H(13)N(3)O(2), using 2-methoxy-benzaldehyde and nicotinic acid hydrazide. Crystal structure analysis revealed specific hydrogen bonding patterns forming molecular chains.

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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:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Nicotinic acid hydrazide derivatives are known for diverse biological activities.
Substituted benzaldehydes are common precursors in organic synthesis.
Understanding intermolecular interactions is crucial for designing functional materials.

Purpose of the Study:

To synthesize and characterize a new organic compound.
To investigate the crystal structure and intermolecular interactions of the title compound.
To explore the potential applications of novel hydrazide derivatives.

Main Methods:

Synthesis via condensation reaction of 2-methoxy-benzaldehyde and nicotinic acid hydrazide in methanol.
Single crystal X-ray diffraction for structural determination.
Analysis of hydrogen bonding networks (N-H⋯O, C-H⋯O, C-H⋯N).

Main Results:

Successful synthesis of the title compound C(14)H(13)N(3)O(2).
The crystal structure exhibits a dihedral angle of 5.9(3)° between the benzene and pyridine rings.
Molecules form chains along the c-axis through intermolecular N-H⋯O hydrogen bonds, further linked by C-H⋯O and C-H⋯N bonds.

Conclusions:

The study successfully synthesized and characterized a novel organic compound.
The crystal structure reveals specific intermolecular interactions that dictate the solid-state arrangement.
The findings provide insights into the structure-property relationships of nicotinic acid hydrazide derivatives.