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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
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.
2.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.2K
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...
3.2K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.7K
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.
3.7K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.3K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.3K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.8K
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...
1.8K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

7.5K
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
7.5K

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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N,N'-Di-benzyl-ethyl-enedi-ammonium dichloride.

Mary Helene Marmande1, Bailey N Baxter1, Matthias Zeller2

  • 1University of South Alabama, Department of Chemistry 6040 USA Drive South Mobile Alabama 36608 USA.

Acta Crystallographica. Section E, Crystallographic Communications
|December 23, 2024
PubMed
Summary

An unintended product, N,N'-di-benzyl-ethyl-enedi-ammonium dichloride, was isolated during a Curtius rearrangement experiment. This highlights the value of undergraduate research, even when outcomes are unexpected.

Keywords:
crystal structurehydrogen bondingmodulationpseudo-translationside reaction

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Chemical Education

Background:

  • The Curtius rearrangement is a valuable synthetic tool for creating medicinally relevant compounds.
  • Course-Based Undergraduate Research Experiences (CUREs) aim to integrate authentic research into laboratory courses.
  • Unforeseen reaction products can offer valuable learning opportunities and insights into reaction mechanisms.

Purpose of the Study:

  • To report the isolation and crystalline structure of N,N -di-benzyl-ethyl-enedi-ammonium dichloride.
  • To illustrate the importance of unexpected outcomes in undergraduate synthetic organic chemistry research.
  • To analyze the structural features and intermolecular interactions of the synthesized compound.

Main Methods:

  • Attempted Curtius rearrangement using benzyl-amine and 1,2-di-chloro-ethane.
  • Isolation and purification of the unintended product, N,N -di-benzyl-ethyl-enedi-ammonium dichloride.
  • Single-crystal X-ray diffraction analysis to determine the solid-state structure.

Main Results:

  • N,N -di-benzyl-ethyl-enedi-ammonium dichloride was successfully isolated as an unintended product.
  • The crystalline structure revealed an all-trans methylene-ammonium backbone.
  • Strong N-H⋯Cl hydrogen bonds and C-H⋯Cl interactions resulted in a layered structure with pseudo-translational symmetry.

Conclusions:

  • The reaction outcome underscores the role of solvent competition in organic synthesis.
  • This unexpected result provided a valuable learning experience within a CURE setting.
  • The detailed structural analysis contributes to understanding supramolecular assembly driven by hydrogen bonding and C-H⋯Cl interactions.