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Related Concept Videos

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.
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 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).
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...
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...
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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2-(4-Methyl-phen-yl)benzonitrile.

M S Siddegowda, Jerry P Jasinski, James A Golen

    Acta Crystallographica. Section E, Structure Reports Online
    |August 13, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study analyzes the crystal structure of C(14)H(11)N, revealing a 44.6° dihedral angle between its benzene rings. Crystal packing is reinforced by π-π stacking interactions.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding molecular geometry and intermolecular forces is crucial for predicting material properties.
    • Aromatic compounds exhibit unique packing behaviors due to π-electron systems.

    Purpose of the Study:

    • To determine the precise three-dimensional structure of the title compound, C(14)H(11)N.
    • To investigate the intermolecular interactions governing its crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to analyze the molecular and crystal structure.
    • Geometric parameters, including dihedral angles and intermolecular distances, were calculated.

    Main Results:

    • The dihedral angle between the two benzene rings in C(14)H(11)N was determined to be 44.6(7)°.
    • Crystal packing is characterized by weak intermolecular π-π stacking interactions.
    • Centroid-centroid distances for π-π stacking were measured at 3.8172(12) Å and 3.9349(12) Å.

    Conclusions:

    • The non-planar conformation of C(14)H(11)N is a key structural feature.
    • Intermolecular π-π stacking plays a significant role in stabilizing the crystal lattice.
    • These findings contribute to the understanding of structure-property relationships in organic crystalline materials.