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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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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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.
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NMR Spectroscopy of Benzene Derivatives01:37

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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...
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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...
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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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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).
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1-Fluoro-4-[(E)-2-nitro-vin-yl]benzene.

S Sreenivasa1, M S Nanjundaswamy2, K E Manojkumar1

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Acta Crystallographica. Section E, Structure Reports Online
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Summary

This study details the crystal structure of a fluorinated organic compound, C8H6FNO2. Molecular analysis reveals a nearly planar structure with trans conformation and disordered side chains, forming crystal chains via hydrogen bonds.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
  • Fluorinated organic compounds are of interest due to their unique electronic properties and applications in various fields.
  • Crystal engineering aims to design materials with specific properties by controlling intermolecular interactions.

Purpose of the Study:

  • To determine and analyze the crystal structure of the title compound, C8H6FNO2.
  • To investigate the molecular conformation and intermolecular interactions within the crystal lattice.
  • To provide foundational data for potential applications of this fluorinated organic compound.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of the crystal structure included assessing planarity, bond conformations, and atomic disorder.
  • Identification and analysis of intermolecular interactions, such as C-H⋯O hydrogen bonds, were performed.

Main Results:

  • The title compound, C8H6FNO2, exhibits a nearly planar molecular geometry with a root-mean-square deviation of 0.019 Å for non-hydrogen atoms.
  • A trans conformation was observed across the central C=C bond.
  • Disorder in the side chain was quantified, with carbon and hydrogen atoms occupying two sets of sites in a 0.56:0.44 ratio.
  • Intermolecular C-H⋯O interactions were identified, leading to the formation of C(5) chains propagating along the [001] direction.

Conclusions:

  • The crystal structure of C8H6FNO2 is elucidated, revealing key geometric and conformational features.
  • The observed intermolecular interactions dictate the crystal packing, forming extended chain structures.
  • This structural information serves as a basis for further research into the chemical and physical properties of this compound.