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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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Related Experiment Video

Updated: Jun 1, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

1,4-Bis(2-pyridylmeth-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

Structural analysis of C(18)H(16)N(2)O(2) reveals a phenyl-ene ring at an inversion center. Molecules form linear chains via C-H⋯N hydrogen bonds in the crystal structure.

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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding molecular arrangements is crucial for predicting material properties.
  • Hydrogen bonding plays a significant role in crystal packing and supramolecular assembly.
  • The study focuses on a specific organic compound with potential applications.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C(18)H(16)N(2)O(2).
  • To investigate the intermolecular interactions governing crystal packing.
  • To characterize the spatial relationship between the phenyl-ene and pyridyl rings.

Main Methods:

  • Single-crystal X-ray diffraction was employed for structural determination.
  • Analysis of bond lengths, bond angles, and dihedral angles.
  • Identification and analysis of intermolecular hydrogen bonding interactions (C-H⋯N).

Main Results:

  • The crystal structure was successfully determined for C(18)H(16)N(2)O(2).
  • The phenyl-ene ring is situated at an inversion center within the molecule.
  • A dihedral angle of 39.9° was observed between the phenyl-ene and pyridyl rings.
  • Intermolecular C-H⋯N hydrogen bonds link adjacent molecules into linear chains along the a axis.

Conclusions:

  • The crystal structure provides detailed insights into the solid-state arrangement of C(18)H(16)N(2)O(2).
  • The observed hydrogen bonding network dictates the formation of one-dimensional chains.
  • This structural information is fundamental for further studies on the compound's physical and chemical properties.