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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.

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.

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

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...

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Related Experiment Video

Updated: Jun 1, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

N-(3,4-Dichloro-phen-yl)thio-urea.

Hai-Bo Shi, Wei-Xiao Hu, Yan-Fang Lin

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a dichlorinated thiourea derivative. Molecules form a 3D network through hydrogen bonds involving sulfur and chlorine atoms.

Area of Science:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Thiourea derivatives are important in medicinal chemistry and materials science.
Understanding the solid-state structure is crucial for predicting chemical properties and designing new materials.

Purpose of the Study:

To elucidate the crystal structure of a novel dichlorinated thiourea compound.
To investigate the intermolecular interactions governing the solid-state packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and dihedral angles provided structural insights.
Intermolecular interactions, including hydrogen bonding, were identified and analyzed.

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Published on: March 6, 2019

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Published on: March 6, 2019

Main Results:

The crystal structure of C(7)H(6)Cl(2)N(2)S was determined.
A significant dihedral angle of 66.77° was observed between the benzene ring and the thiourea fragment.
A three-dimensional network was formed via intermolecular hydrogen bonds (N-H⋯S and N-H⋯Cl).

Conclusions:

The compound exhibits a distinct non-planar conformation due to the relative orientation of the aromatic and thio-urea moieties.
The observed hydrogen bonding network dictates the supramolecular architecture in the solid state.
This structural information is valuable for understanding structure-property relationships in related thiourea derivatives.