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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.
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.
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...
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
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

Ethyl 4-fluoro-3-nitro-benzoate.

Shivanagere Nagojappa Narendra Babu, Aisyah Saad Abdul Rahim, Hasnah Osman

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

    The crystal structure of C(9)H(8)FNO(4) reveals intermolecular interactions forming dimers. These dimers further assemble into chains stacked along the c axis, detailing its solid-state arrangement.

    Area of Science:

    • Crystallography
    • Solid-state chemistry
    • Molecular interactions

    Background:

    • Understanding the crystal packing and intermolecular forces of organic compounds is crucial for predicting their physical and chemical properties.
    • The specific arrangement of molecules in the solid state influences material characteristics, including solubility, stability, and reactivity.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(9)H(8)FNO(4).
    • To identify and characterize the intermolecular interactions governing the compound's solid-state assembly.
    • To describe the hierarchical organization of molecules from dimers to chains and their stacking arrangement.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.

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

    Published on: June 28, 2011

    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)

    Published on: June 20, 2014

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    Last 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

    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

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
    06:34

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

    Published on: June 20, 2014

  • Analysis of intermolecular contacts, including C-H⋯O interactions, was performed.
  • Crystal structure visualization and analysis of packing motifs were conducted.

    • Main Results:

    • The crystal structure of C(9)H(8)FNO(4) was successfully determined.
    • Specific C-H⋯O intermolecular interactions were identified, leading to the formation of dimers with R(2)(2)(10) hydrogen bonding motifs.
    • These dimers were observed to arrange into one-dimensional chains aligned parallel to the b crystallographic axis.
    • The chains were further observed to stack along the c crystallographic axis, defining the overall crystal packing.

    Conclusions:

    • The study successfully characterized the crystal structure of C(9)H(8)FNO(4).
    • The formation of dimers via C-H⋯O interactions and their subsequent arrangement into chains and stacked layers dictate the compound's solid-state architecture.
    • This detailed structural information provides a foundation for understanding the material properties of C(9)H(8)FNO(4).