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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

6.0K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
6.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.4K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
4.4K
Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

9.9K
Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
9.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

8.1K
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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Peripherally Hexasulfanylated Subporphyrins.

Kota Yoshida1, Atsuhiro Osuka2

  • 1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.

Chemistry, an Asian Journal
|March 31, 2015
PubMed
Summary

Researchers synthesized novel hexasulfanylated subporphyrins through nucleophilic aromatic substitution reactions. These compounds exhibit unique structural and electronic properties, with one effectively capturing C60 fullerenes.

Keywords:
SNAr reactionfullerenesporphyrinoidssubporphyrinssulfanylation

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Subporphyrins are macrocyclic compounds with unique photophysical and electronic properties.
  • Functionalization of subporphyrin scaffolds is crucial for tuning their characteristics.
  • Exploring novel synthetic routes to substituted subporphyrins is an active area of research.

Purpose of the Study:

  • To synthesize novel hexasulfanylated meso-triphenyl subporphyrins.
  • To characterize the structural and conformational properties of these new compounds.
  • To investigate the electronic effects of sulfanyl substituents and their ability to interact with fullerenes.

Main Methods:

  • Chlorination of meso-triphenyl subporphyrin using N-chlorosuccinimide.
  • Nucleophilic aromatic substitution (S(N)Ar) reactions with thiols.
  • Single-crystal X-ray diffraction for structural determination.
  • (1)H NMR spectroscopy for conformational analysis.
  • UV-Vis absorption spectroscopy, cyclic voltammetry, and DFT calculations for electronic properties.

Main Results:

  • Hexachlorinated meso-triphenyl subporphyrin was synthesized and converted to hexasulfanylated derivatives (5-8).
  • X-ray crystallography confirmed the structures of compounds 5-8.
  • (1)H NMR revealed restricted rotation of meso-phenyl groups and varied conformational flexibility of β-sulfanyl groups.
  • Electronic properties were modulated by sulfanyl substituents, with the order of effect 5>6>7>8.
  • Subporphyrin 8 demonstrated effective 1:1 capture of C60 fullerenes.

Conclusions:

  • Novel hexasulfanylated subporphyrins were successfully synthesized and characterized.
  • The study elucidates the impact of sulfanyl substituents on subporphyrin structure and electronic properties.
  • Subporphyrin 8 shows potential for fullerene complexation, relevant for molecular recognition and materials science.