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Crown Ethers02:36

Crown Ethers

5.1K
Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether...
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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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...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
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...
4.0K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

5.7K
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.
5.7K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

7.3K
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...
7.3K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

7.7K
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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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Halogen-substituted benzylamine crown ether inclusion complexes.

Yan Juan Wang1, Yao Zhang2, Yuan Yuan Tang1

  • 1Ordered Matter Science Research Center, Nanchang University, Nanchang 330031, People's Republic of China.

Acta Crystallographica. Section C, Structural Chemistry
|March 13, 2025
PubMed
Summary
This summary is machine-generated.

This study explores the halogenation effect on benzylamine host-guest compounds with 18-crown-6. The research demonstrates how varying halogen substituents influence crystal structures and intermolecular interactions in supramolecular chemistry.

Keywords:
18-crown-6DMSAclathratecrystal structurehalogenation effectweak intermolecular interaction di(methanesulfonyl)ammonium

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Area of Science:

  • Supramolecular Chemistry
  • Crystal Engineering
  • Host-Guest Chemistry

Background:

  • Noncovalent interactions are crucial in supramolecular chemistry and crystal engineering.
  • Crown-ether-based host-guest inclusion compounds are of significant interest.
  • The H/F substitution strategy offers a pathway to explore the halogenation effect.

Purpose of the Study:

  • To investigate the impact of halogenation on benzylamine host-guest compounds.
  • To synthesize and characterize four novel halogenated benzylamine-18-crown-6-di(methanesulfonyl)amidate complexes.
  • To explore the self-assembly of supramolecular architectures driven by intermolecular interactions.

Main Methods:

  • Utilized the halogenation effect strategy by substituting hydrogen atoms with halogens (F, Cl, Br, I) on the para-site of benzylamine.
  • Synthesized four distinct host-guest inclusion compounds: [(4-FBA)(18-crown-6)][DMSA], [(4-ClBA)(18-crown-6)][DMSA], [(4-BrBA)(18-crown-6)][DMSA], and [(4-IBA)(18-crown-6)][DMSA].
  • Determined crystal structures, with compound 1 crystallizing in space group P21 and compounds 2-4 in space group P21/n.

Main Results:

  • Successfully synthesized four halogenated benzylamine-18-crown-6-di(methanesulfonyl)amidate complexes.
  • Observed distinct crystallization behaviors based on the type of halogen substituent.
  • Demonstrated the role of extensive intermolecular interactions in the self-assembly of diverse supramolecular architectures.

Conclusions:

  • The halogenation effect is a viable strategy for designing novel supramolecular compounds.
  • Halogen substitution significantly influences the crystal packing and supramolecular assembly.
  • These findings contribute to the understanding of host-guest interactions and crystal engineering.