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Related Concept Videos

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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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.
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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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Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
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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.
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This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.
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[18]Annulene put into a new perspective.

Dominik Lungerich1, Alexey V Nizovtsev2, Frank W Heinemann2

  • 1Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Organic Chemistry II, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestraße 42, 91054, Erlangen, Germany. norbert.jux@fau.de.

Chemical Communications (Cambridge, England)
|March 9, 2016
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Summary

Researchers studied the crystal structure of [18]annulene, finding a unique herringbone packing. This revealed how solvent molecules stabilize solid annulenes, offering new insights into their structure and properties.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Solid-State Chemistry

Background:

  • [18]Annulene and its derivatives are important macrocyclic organic compounds.
  • Understanding the solid-state packing of annulenes is crucial for predicting their properties.

Purpose of the Study:

  • To investigate the crystal structure of [18]annulene.
  • To elucidate the role of solvent molecules in stabilizing solid annulenes.

Main Methods:

  • X-ray crystallography was employed to analyze the crystal structure.
  • Co-crystallization of hexadehydro[18]annulene with benzene was performed.

Main Results:

  • A face-to-face stacking of [18]annulene molecules at 3.16 Å was observed.
  • A herringbone-like crystal packing arrangement was identified.
  • The study demonstrated the stabilizing effect of intercalated benzene molecules.

Conclusions:

  • The crystal structure of [18]annulene reveals specific intermolecular interactions.
  • Intercalated solvent molecules play a significant role in the stabilization of solid annulene structures.