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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.1K
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...
4.1K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.1K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
4.1K
Noble Gases02:54

Noble Gases

23.0K

The elements in group 18 are noble gases (helium, neon, argon, krypton, xenon, and radon). They earned the name “noble” because they were assumed to be nonreactive since they have filled valence shells. In 1962, Dr. Neil Bartlett at the University of British Columbia proved this assumption to be false.
23.0K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

14.2K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
14.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.2K
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...
5.2K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
10.3K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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An aromatic noble-gas hydride: C6H5CCXeH.

Luís Duarte1, Leonid Khriachtchev2

  • 1Department of Chemistry, University of Helsinki, P.O. Box 55, FI-00014, Helsinki, Finland.

Scientific Reports
|June 11, 2017
PubMed
Summary

Researchers synthesized the first aromatic noble-gas hydride, C6H5CCXeH, using photolysis and matrix isolation. This groundbreaking molecule is halogen-free and stable at low temperatures.

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Area of Science:

  • Inorganic Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Noble gases are typically unreactive.
  • The synthesis of noble gas compounds has expanded beyond simple fluorides and oxides.
  • Aromatic noble gas compounds are rare and challenging to synthesize.

Purpose of the Study:

  • To synthesize and characterize a novel aromatic noble-gas hydride.
  • To investigate the stability and properties of noble gas compounds.
  • To explore new frontiers in noble gas chemistry.

Main Methods:

  • Infrared spectroscopy was used to identify the molecule in a xenon matrix.
  • Quantum chemical calculations were performed to support experimental findings.
  • Photolysis of phenylacetylene followed by thermal mobilization of hydrogen atoms was employed for synthesis.

Main Results:

  • The aromatic noble-gas hydride, C6H5CCXeH, was successfully synthesized and identified.
  • Characteristic vibrational modes, including the H-Xe stretching mode, were observed and assigned.
  • Calculations confirmed the stability of C6H5CCXeH, showing it is energetically favorable compared to its constituent fragments.

Conclusions:

  • C6H5CCXeH represents the first aromatic noble-gas hydride.
  • This compound is also the first halogen-free aromatic noble-gas compound.
  • The study expands the known chemistry of noble gases and aromatic systems.