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Related Concept Videos

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...
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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:
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives01:15

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
Diazonium Group Substitution: –OH and –H01:19

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.

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Related Experiment Video

Updated: May 14, 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

Phenyl acridine-9-carboxyl-ate.

Michał Wera1, Damian Trzybiński, Karol Krzymiński

  • 1Faculty of Chemistry, University of Gdańsk, J. Sobieskiego 18, 80-952 Gdańsk, Poland.

Acta Crystallographica. Section E, Structure Reports Online
|February 21, 2013
PubMed
Summary

This study details the crystal structure of a C(20)H(13)NO(2) compound, revealing specific molecular orientations and π-π interactions. The arrangement forms layered structures through various intermolecular forces, influencing crystal packing.

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Published on: August 22, 2018

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding molecular packing is crucial for predicting material properties.
  • Acridine derivatives are known for their diverse applications in materials science and pharmaceuticals.
  • Detailed structural analysis provides insights into intermolecular forces and crystal engineering.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C(20)H(13)NO(2).
  • To investigate the molecular orientation and intermolecular interactions within the crystal lattice.
  • To describe the supramolecular assembly and packing motifs.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided information on molecular geometry.
  • Intermolecular interactions, including π-π stacking and C-H⋯π interactions, were identified and quantified.

Main Results:

  • The dihedral angle between the acridine and benzene rings is 6.4(2)°.
  • The carboxyl group is oriented at 83.6(2)° relative to the acridine skeleton.
  • Molecules form stacks along the b axis driven by π-π interactions (3.536(2)-3.894(2) Å).
  • Layered structures are formed via C-H⋯π interactions, creating double layers with specific acridine unit orientations (79.6(2)° in inversely oriented stacks).

Conclusions:

  • The crystal structure of C(20)H(13)NO(2) exhibits a unique packing arrangement driven by π-π and C-H⋯π interactions.
  • The specific orientation of the acridine and benzene rings, along with the carboxyl group, dictates the observed supramolecular architecture.
  • This detailed structural understanding can inform the design of new organic materials with tailored properties.