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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...
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...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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Related Experiment Video

Updated: Jun 1, 2026

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)

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4-(1-Naphth-yl)benzonitrile.

Carlos F Lima, Ligia R Gomes, Luís M N B F Santos

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

    This study details the crystal structure of C(17)H(11)N, revealing weak C-H⋯N hydrogen bonds and C-H⋯π interactions. These forces create a three-dimensional molecular network in the crystal lattice.

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    Published on: January 21, 2020

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding intermolecular forces is crucial for predicting crystal packing and material properties.
    • The compound C(17)H(11)N presents an interesting molecular structure for studying weak interactions.
    • Crystal engineering relies on identifying and controlling non-covalent interactions.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(17)H(11)N.
    • To identify and characterize the intermolecular interactions present in the crystal lattice.
    • To understand the packing arrangement and network formation in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond distances, angles, and non-covalent interactions was performed.
    • Dihedral angles between aromatic ring systems were precisely measured.

    Main Results:

    • The title compound, C(17)H(11)N, crystallizes with two molecules in the asymmetric unit.
    • Weak C-H⋯N hydrogen bonds and C-H⋯π interactions were identified as key intermolecular forces.
    • The dihedral angles between the benzene and naphthalene ring systems were found to be approximately 60.28° and 60.79°.
    • These interactions result in the formation of a three-dimensional molecular network.

    Conclusions:

    • The crystal structure of C(17)H(11)N is stabilized by a combination of weak hydrogen bonds and π-π stacking interactions.
    • The observed dihedral angles influence the overall molecular conformation and packing.
    • The study provides insights into the supramolecular assembly of organic molecules driven by weak non-covalent interactions.