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Related Concept Videos

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.
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...
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).
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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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...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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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...

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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4,4'-Bipyridine-2,3,4,5,6-penta-fluoro-benzoic acid (1/2).

Xiangdong Zhang1, Lijuan Wang, Chunhua Ge

  • 1College of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study details a 1:2 adduct formed between 4,4'-bipyridine and pentafluorobenzoic acid. The crystal structure reveals hydrogen bonds and other interactions holding the molecules together.

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Area of Science:

  • Crystal engineering
  • Supramolecular chemistry
  • Organic chemistry

Background:

  • 4,4 -bipyridine is a versatile ligand in coordination chemistry.
  • Pentafluorobenzoic acid is a fluorinated organic acid with potential applications in materials science.
  • Adduct formation is a key strategy for creating novel crystalline materials.

Purpose of the Study:

  • To synthesize and characterize a novel 1:2 adduct of 4,4 -bipyridine and pentafluorobenzoic acid.
  • To investigate the intermolecular interactions governing the crystal structure of the adduct.
  • To explore the potential of such adducts in crystal engineering.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Crystallographic symmetry analysis.
  • Analysis of intermolecular interactions (hydrogen bonds, van der Waals forces).

Main Results:

  • A 1:2 adduct of 4,4 -bipyridine and pentafluorobenzoic acid was successfully synthesized and characterized.
  • The crystal structure features a crystallographic twofold axis generating the complete 4,4 -bipyridine molecule.
  • Intermolecular O-H⋯N hydrogen bonds and C-H⋯O, C-H⋯F, and F⋯F interactions stabilize the crystal lattice.

Conclusions:

  • The study successfully elucidated the crystal structure of a novel 1:2 adduct.
  • The findings highlight the role of hydrogen bonding and other non-covalent interactions in directing supramolecular assembly.
  • This work contributes to the understanding of crystal engineering principles for designing functional organic materials.