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Related Concept Videos

Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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...
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).
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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1,4-Bis(pyridin-3-ylmeth-oxy)benzene.

Jin-Sheng Gao1, Ying Liu, Shuang Zhang

  • 1College of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China.

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

This study details the crystal structure of a new organic compound, C(18)H(16)N(2)O(2). Molecular analysis reveals specific dihedral angles between aromatic rings and intermolecular hydrogen bonds influencing crystal packing.

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Published on: December 16, 2019

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding molecular interactions is crucial for designing novel materials.
  • Crystal structure analysis provides insights into intermolecular forces and packing arrangements.
  • The title compound, C(18)H(16)N(2)O(2), represents a potential building block for advanced organic materials.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(18)H(16)N(2)O(2).
  • To analyze the geometric parameters, including dihedral angles between aromatic rings.
  • To identify and characterize intermolecular interactions, such as hydrogen bonds, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
  • The asymmetric unit was analyzed to understand the fundamental building block of the crystal.
  • Dihedral angles and hydrogen bonding networks were geometrically analyzed.

Main Results:

  • The asymmetric unit contains one half-molecule, indicating a centrosymmetric crystal structure.
  • A significant dihedral angle of 66.8(1)° was observed between the central benzene ring and the two outer aromatic rings.
  • Weak intermolecular C-H⋯N hydrogen bonds were identified, linking molecules into sheets parallel to the (104) crystallographic plane.

Conclusions:

  • The crystal structure of C(18)H(16)N(2)O(2) is characterized by specific aromatic ring orientations and a network of C-H⋯N hydrogen bonds.
  • These intermolecular interactions dictate the formation of sheet-like structures in the solid state.
  • The findings contribute to the understanding of structure-property relationships in organic crystalline materials.