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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.
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...
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...
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...
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...
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

3-Fluoro-N-(p-tol-yl)benzamide.

Aamer Saeed, Rasheed Ahmad Khera, Kazuma Gotoh

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the crystal structure of C(14)H(12)FNO, revealing specific dihedral angles between its aromatic rings and amide plane. Molecules form hydrogen-bonded networks, stacking along the crystal

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding molecular arrangements in organic compounds is crucial for predicting material properties.
    • Crystal structure analysis provides detailed insights into intermolecular interactions and solid-state behavior.

    Purpose of the Study:

    • To elucidate the three-dimensional molecular structure of the title compound, C(14)H(12)FNO.
    • To investigate the dihedral angles and intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles was performed.

    Main Results:

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    Published on: June 28, 2011

    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

    Published on: November 23, 2016

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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
    08:43

    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

    Published on: January 19, 2016

    Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)
    08:33

    Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)

    Published on: June 28, 2011

    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

    Published on: November 23, 2016

  • The crystal structure of C(14)H(12)FNO was determined, revealing specific dihedral angles: 28.6(2)° and 37.5(2)° between the amide plane and the fluoro-benzene and methyl-benzene units, respectively.
  • A dihedral angle of 65.69(10)° was observed between the two benzene ring planes.
  • Molecules are interconnected via N-H⋯O hydrogen bonds, leading to stacking along the b-axis.

    • Conclusions:

    • The study provides a precise description of the molecular geometry and packing in the crystal structure of C(14)H(12)FNO.
    • The identified hydrogen bonding and stacking interactions are key features governing the solid-state architecture.