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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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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...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Trispyrazol-1-ylmethane.

Tobias Kerscher1, Philipp Pust, Richard Betz

  • 1Ludwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13 (Haus D), 81377 München, Germany.

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

This study details the crystal structure of a nitrogen-rich compound, C(10)H(10)N(6). Weak hydrogen bonds form layers, revealing a new polymorph distinct from a previously documented ortho-rhom-bic form.

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Area of Science:

  • Crystallography
  • Materials Science
  • Supramolecular Chemistry

Background:

  • The title compound, C(10)H(10)N(6), is a nitrogen-rich molecule.
  • Understanding its solid-state structure is crucial for potential applications.

Purpose of the Study:

  • To characterize a specific polymorph of the title compound, C(10)H(10)N(6).
  • To investigate the intermolecular interactions governing its crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of non-covalent interactions, specifically C-H⋯N hydrogen bonds, was performed.

Main Results:

  • The crystal structure reveals the formation of layered assemblies.
  • Weak C-H⋯N contacts (2.49–2.59 Å) between pyrazole nitrogen atoms and hydrogen atoms facilitate layer formation.
  • These layers are oriented perpendicular to the [100] crystallographic direction.

Conclusions:

  • The identified crystal structure represents a distinct polymorph of C(10)H(10)N(6).
  • The C-H⋯N interactions play a significant role in directing the supramolecular architecture.
  • This finding adds to the structural understanding of nitrogen-rich compounds and their potential for layered materials.