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Related Concept Videos

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.
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:
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...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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 Amines01:19

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 amide...
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.

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Related Experiment Video

Updated: May 19, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

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

Published on: November 23, 2016

N-[4-(4-Nitro-phen-oxy)phen-yl]acetamide.

Asifa Nigar, Zareen Akhter, M Nawaz Tahir

    Acta Crystallographica. Section E, Structure Reports Online
    |August 21, 2012
    PubMed
    Summary

    This study details the crystal structure of C(14)H(12)N(2)O(4), revealing distinct molecular orientations and hydrogen bonding. These findings contribute to understanding crystal packing and intermolecular interactions in organic compounds.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Solid-State Chemistry

    Background:

    • Understanding molecular arrangement in crystals is crucial for predicting material properties.
    • Organic compounds with nitro and acetamide groups exhibit diverse crystal structures.
    • Intermolecular interactions dictate crystal packing and stability.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(14)H(12)N(2)O(4).
    • To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
    • To characterize the hydrogen bonding and π-π interactions present.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided conformational insights.

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  • Identification and analysis of hydrogen bonds (N-H⋯O, C-H⋯O) and π-π stacking interactions were performed.
  • Main Results:

    • The asymmetric unit contains two unique molecules differing in acetamide substituent orientation (dihedral angles 44.77° and 19.06°).
    • Significant dihedral angles between benzene rings were observed (64.46° and 80.84°).
    • Classical N-H⋯O hydrogen bonds formed C(4) chains, further linked by C-H⋯O contacts forming R(2)(2)(10) rings. π-π interactions between nitro-substituted benzene rings were noted (3.5976 Å).

    Conclusions:

    • The crystal structure of C(14)H(12)N(2)O(4) is characterized by distinct molecular conformations and specific intermolecular interactions.
    • Hydrogen bonding and π-π stacking play significant roles in stabilizing the crystal lattice.
    • The findings provide valuable data for structure-property relationship studies in related organic materials.