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Related Concept Videos

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.
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...
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).
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).
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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1,3-Dibenz-yloxy-5-(bromo-meth-yl)benzene.

Peihua Zhu1, Yanfang Zhao, Haiyan Chen

  • 1School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, People's Republic of China.

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

This study details the molecular structure of a brominated organic compound, C(21)H(19)BrO(2). It reveals specific dihedral angles between its benzene rings and the conformation of its O-CH(2) bonds.

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Area of Science:

  • Crystallography and Molecular Structure Analysis
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Crystallographic studies provide precise structural data, including bond lengths, bond angles, and dihedral angles, which are fundamental to molecular characterization.

Purpose of the Study:

  • To elucidate the precise three-dimensional molecular structure of the title compound, C(21)H(19)BrO(2).
  • To determine the spatial arrangement of the benzene rings and the conformation of the O-CH(2) groups within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to collect diffraction data.
  • The crystal structure was solved and refined using standard crystallographic techniques.

Main Results:

  • The crystal structure of C(21)H(19)BrO(2) was determined.
  • Significant dihedral angles of 50.28(5)° and 69.75(2)° were measured between the central benzene ring and the two peripheral rings.
  • The O-CH(2) bonds were found to lie in the plane of the central benzene ring, adopting a syn-anti conformation.

Conclusions:

  • The molecular structure of C(21)H(19)BrO(2) is characterized by distinct inter-ring dihedral angles and a specific syn-anti conformation of the O-CH(2) groups.
  • These structural features provide insights into the molecule's conformation in the solid state, potentially influencing its physical and chemical behavior.