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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
Preparation of 1° Amines: Gabriel Synthesis01:28

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 of Nitriles01:12

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...
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.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...

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Related Experiment Video

Updated: Jun 1, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

1-(4-Fluoro-phen-yl)thio-urea.

Aamer Saeed, Uzma Shaheen, Ulrich Flörke

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a fluorinated thio-urea compound. Molecular twisting and hydrogen bonds create layered sheet structures in the solid state.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding molecular interactions is crucial for designing new materials.
    • Crystal engineering utilizes intermolecular forces to build desired structures.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C(7)H(7)FN(2)S.
    • To investigate the molecular conformation and intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of torsion angles and hydrogen bonding networks was performed.

    Main Results:

    • The title compound exhibits a twisted conformation between the aromatic ring and the thio-urea moiety (torsion angle C-C-N-C7 = 44.6°).
    • Intermolecular hydrogen bonds (N-H⋯S and N-H⋯F) were identified, forming infinite sheets stacked along the c-axis.

    Conclusions:

    • The crystal packing is dictated by a combination of molecular conformation and specific hydrogen bonding patterns.
    • The observed sheet structure provides insights into the solid-state properties of fluorinated thio-urea derivatives.