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Related Concept Videos

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...
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.
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...
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).
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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3-(2-Bromo-acet-yl)phenyl benzoate.

Sachin P Ambekar1, H C Devarajegowda, J Shylajakumari

  • 1Department of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

This study details the crystal structure of C15H11BrO3, revealing a significant dihedral angle between benzene rings and unique intermolecular interactions like C-H⋯π and C-H⋯O bonds. These interactions form a complex 3D network in the crystal lattice.

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Area of Science:

  • Crystallography
  • Materials Science
  • Organic Chemistry

Background:

  • Understanding molecular packing and intermolecular forces is crucial for predicting material properties.
  • Crystal structure analysis provides fundamental insights into chemical bonding and supramolecular assembly.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C15H11BrO3.
  • To investigate the intermolecular interactions governing the compound's solid-state arrangement.
  • To characterize the network formed by these interactions.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of non-covalent interactions, including hydrogen bonds and halogen bonds, was performed.
  • Dihedral angles and contact distances were measured.

Main Results:

  • The dihedral angle between the benzene rings in C15H11BrO3 was determined to be 72.59(6)°.
  • C-H⋯π contacts were observed, forming inversion dimers.
  • C-H⋯O hydrogen bonds created R2(1)(6) ring motifs, stacking dimers along the b axis.
  • Short intermolecular Br⋯O contacts (3.254(3) Å) linked these stacks into a 3D network.

Conclusions:

  • The crystal structure of C15H11BrO3 is characterized by a specific dihedral angle and a rich network of intermolecular interactions.
  • These interactions, including C-H⋯π, C-H⋯O, and Br⋯O contacts, dictate the formation of a three-dimensional supramolecular architecture.
  • The findings contribute to the understanding of crystal engineering principles for organic molecules.