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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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.
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.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

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Imidazolium fumarate.

Rodolfo Moreno-Fuquen, Javier Ellena, Jahyr E Theodoro

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of an imidazolium fumarate salt, revealing a near-perpendicular orientation between the imidazolium ring and the fumarate anion. Hydrogen bonds link these molecules into a 2D network.

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    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Organic Chemistry

    Background:

    • Imidazolium salts are versatile compounds with applications in various chemical fields.
    • Fumarate anions are dicarboxylic acid derivatives relevant in biological and chemical systems.
    • Understanding the solid-state structure of ionic compounds is crucial for predicting their properties.

    Purpose of the Study:

    • To elucidate the crystal structure of an imidazolium fumarate salt.
    • To investigate the intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
    • To determine the spatial arrangement and orientation of the imidazolium cation and fumarate anion.

    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 detailed structural information.
    • Hydrogen bond analysis identified and characterized the intermolecular interactions present.

    Main Results:

    • The crystal structure of the imidazolium fumarate salt (C(3)H(5)N(2)(+)·C(4)H(3)O(4)(-)) was successfully determined.
    • A significant dihedral angle of 80.98° was observed between the imidazolium ring and the fumarate anion plane.
    • Intermolecular hydrogen bonds (O-H⋯O and N-H⋯O) were identified, forming extended chains and a two-dimensional network.

    Conclusions:

    • The crystal packing is dominated by hydrogen bonding, leading to a robust 2D network structure.
    • The observed dihedral angle suggests a specific conformational preference in the solid state.
    • This structural insight contributes to the understanding of imidazolium-based ionic compounds and their supramolecular assembly.