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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.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Optical properties of (Z)-2-(2-phenylhydrazinylidene)acenaphthen-1(2H)-one: a potential electron donor in organic solar cells.

Acta crystallographica. Section C, Structural chemistry·2017
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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4-(4-Hydroxy-phenyl-diazen-yl)-benzonitrile.

Chao Zhi Zhang1

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

This study reveals that an achiral molecule, C(13)H(9)N(3)O, exhibits chirality in its crystal structure due to intermolecular hydrogen bonding, forming a chain. This finding highlights the importance of crystal packing in determining molecular properties.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Area of Science:

  • Crystallography
  • Molecular Chemistry
  • Organic Chemistry

Background:

  • Chirality is a fundamental property in chemistry and biology.
  • Understanding molecular arrangement in crystals is crucial for predicting material properties.
  • The title compound, C(13)H(9)N(3)O, was synthesized and its crystal structure investigated.

Purpose of the Study:

  • To determine the crystal structure of the title compound C(13)H(9)N(3)O.
  • To investigate the relationship between molecular structure and crystal packing.
  • To analyze the stereochemistry and intermolecular interactions within the crystal.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles.
  • Identification and analysis of intermolecular interactions, specifically hydrogen bonding.

Main Results:

  • The molecule C(13)H(9)N(3)O is achiral but adopts a chiral arrangement in the crystal lattice.
  • The molecule exhibits an E configuration around the N=N bond and is nearly planar (r.m.s. deviation of 0.0439 Å).
  • A small dihedral angle of 2.2(2)° between the two benzene rings was observed.
  • Intermolecular O-H⋯N hydrogen bonds link molecules into a one-dimensional chain.

Conclusions:

  • Crystal packing forces can induce chirality in achiral molecules.
  • The observed hydrogen bonding network plays a significant role in the formation of the chiral crystal structure.
  • This study provides insights into structure-property relationships influenced by intermolecular forces.