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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...
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the more strongly...
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...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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1,4-Bis(4-nitro-styr-yl)benzene.

Phuong-Truc T Pham1

  • 1Department of Chemistry, Penn State Worthington Scranton, 120 Ridge View Drive, Dumore, Pennsylvania 18512, USA.

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

This study details the molecular structure of C(22)H(16)N(2)O(4), revealing its inversion center and tilted aromatic rings. Crystal packing analysis shows van der Waals forces govern stair-like stacking, with specific intermolecular contacts identified.

Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Molecular structure analysis

Background:

  • Understanding the precise arrangement of atoms in organic molecules is crucial for predicting their properties.
  • Crystal packing significantly influences macroscopic material characteristics.
  • Detailed structural analysis provides fundamental insights into intermolecular forces.

Purpose of the Study:

  • To elucidate the complete molecular structure of the title compound, C(22)H(16)N(2)O(4).
  • To investigate the intermolecular interactions and crystal packing arrangement.
  • To identify specific short-range contacts within the crystal lattice.

Main Methods:

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

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  • Analysis of crystallographic data provided information on bond lengths, angles, and molecular symmetry.
  • Intermolecular contacts and packing motifs were examined using crystallographic software.

    • Main Results:

    • The molecule C(22)H(16)N(2)O(4) possesses a crystallographic center of inversion.
    • A notable tilt of 11.85(4)° exists between the central and outer aromatic rings.
    • Crystal packing is dominated by van der Waals interactions, featuring staggered, stair-like stacking of aromatic rings at approximately 3.8 Å separation.
    • The shortest intermolecular contact observed is between an oxygen atom and a vinyl hydrogen atom (approx. 2.42 Å).

    Conclusions:

    • The crystal structure of C(22)H(16)N(2)O(4) is characterized by specific geometric arrangements and intermolecular forces.
    • Van der Waals interactions and pi-stacking play a key role in the observed crystal packing.
    • The identified intermolecular contact provides insight into the molecule's solid-state behavior.