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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.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...

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...

Nomenclature of Aryl and Heterocyclic Amines

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.

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Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

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N-(4-Meth-oxy-2-nitro-phen-yl)acetamide.

James E Hines Iii¹, Curtistine J Deere¹, Poornasai Vaddi¹

¹Department of Environmental Toxicology, Southern University and A&M College, Baton Rouge, LA 70813, USA.

|November 7, 2022

Summary

This summary is machine-generated.

This study analyzes the molecular structure of a phenyl ring compound (C9H10N2O4), detailing how methoxy, nitro, and acetamido groups deviate from planarity. An intramolecular hydrogen bond was observed between the NH group and a nitro group oxygen.

Keywords:

crystal structure hydrogen bonding

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Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Understanding substituent effects on aromatic ring planarity is crucial in organic chemistry.
Aromatic compounds with diverse functional groups exhibit unique electronic and steric properties.

Purpose of the Study:

To investigate the three-dimensional structure of a specific phenyl ring compound (C9H10N2O4).
To quantify the degree of planarity deviation for methoxy, nitro, and acetamido substituents.
To identify intramolecular interactions within the molecule.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular geometry.
Torsion angles were calculated to assess the deviation from planarity for each substituent.
Intramolecular hydrogen bonding was analyzed based on atomic distances and angles.

Main Results:

The methoxy group exhibited minimal deviation from planarity (torsion angle 6.1°).
The nitro group showed a moderate twist (12.8°).
The acetamido group displayed the largest deviation from planarity (25.4°).
An intramolecular N-H⋯O hydrogen bond was identified between the acetamido NH and a nitro group oxygen.

Conclusions:

Substituent identity and position significantly influence the planarity of the phenyl ring.
Intramolecular hydrogen bonding plays a role in stabilizing the non-planar conformation.
The findings contribute to the understanding of structure-property relationships in substituted aromatic systems.