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Diazonium Group Substitution: –OH and –H

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.

Chemical Ionization (CI) Mass Spectrometry

Chemical Ionization (CI) Mass Spectrometry

The molecular ion peak of a molecule in the mass spectrum provides vital information for molecular identification. However, conventional electron impact ionization can lead to the rapid dissociation of some molecular ions before they reach the detector. A milder ionization method is required to increase the lifetime of such ionized analyte molecules. Chemical ionization (CI) is a gas-phase protonation reaction useful for mass-analyzing analyte molecules that are easily protonated to yield the...

Formation of Halohydrin from Alkenes

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

Polyprotic Acids

Polyprotic Acids

Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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

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.

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1-Methyl-hydrazinium picrate.

Xiao-Gang Mu¹, Xuan-Jun Wang, Youzhi Zhang

¹No. 503 Faculty, Xi'an Research Institute of High Technology, Hongqing Town, Xi'an 710025, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|December 27, 2011

Summary

This study details the crystal structure of a novel salt, revealing specific dihedral angles of nitro groups relative to the benzene ring. The findings illustrate the formation of a two-dimensional hydrogen-bonded network in its crystalline state.

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Area of Science:

Crystallography
Materials Science
Chemical Physics

Background:

Understanding the molecular arrangement and intermolecular interactions in crystalline salts is crucial for predicting their physical and chemical properties.
Salts containing nitroaromatic anions are of interest due to their potential applications in energetic materials and as precursors in organic synthesis.

Purpose of the Study:

To elucidate the crystal structure of the salt formed between a nitrogen-containing cation and a nitroaromatic anion.
To analyze the spatial arrangement of nitro groups and their orientation with respect to the aromatic ring.
To investigate the hydrogen bonding network responsible for the crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the salt.
Analysis of dihedral angles was performed to quantify the deviation of nitro groups from the benzene ring plane.
Hydrogen bonding interactions were identified and characterized using crystallographic data.

Main Results:

The crystal structure of the salt, [CH(7)N(2)](+)[C(6)H(2)N(3)O(7)](-), was successfully determined.
Dihedral angles between the three nitro groups and the benzene ring plane were found to be 22.4(2)°, 35.3(2)°, and 2.8(2)°.
A two-dimensional network of N-H⋯O and N-H⋯N hydrogen bonds was observed, parallel to the (10[Formula: see text]) plane.

Conclusions:

The crystal structure reveals a specific non-planar arrangement of nitro substituents on the aromatic ring.
The identified hydrogen bonding network plays a significant role in stabilizing the crystal lattice.
These findings contribute to the understanding of structure-property relationships in nitroaromatic salts.