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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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.
Removing one hydrogen from the intervening CH2 group...
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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
17.3K
Network Covalent Solids02:18

Network Covalent Solids

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Network covalent solids contain a three-dimensional network of covalently bonded atoms as found in the crystal structures of nonmetals like diamond, graphite, silicon, and some covalent compounds, such as silicon dioxide (sand) and silicon carbide (carborundum, the abrasive on sandpaper). Many minerals have networks of covalent bonds.
To break or to melt a covalent network solid, covalent bonds must be broken. Because covalent bonds are relatively strong, covalent network solids are typically...
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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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.
Due to the absence of continuous...
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Crystal Field Theory - Octahedral Complexes02:58

Crystal Field Theory - Octahedral Complexes

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Crystal Field Theory
To explain the observed behavior of transition metal complexes (such as colors), a model involving electrostatic interactions between the electrons from the ligands and the electrons in the unhybridized d orbitals of the central metal atom has been developed. This electrostatic model is crystal field theory (CFT). It helps to understand, interpret, and predict the colors, magnetic behavior, and some structures of coordination compounds of transition metals.
CFT focuses on...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Compressed Corannulene in a Molecular Cage.

Bernd M Schmidt1, Takafumi Osuga1, Tomohisa Sawada1

  • 1Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.

Angewandte Chemie (International Ed. in English)
|December 15, 2015
PubMed
Summary

Self-assembled coordination cages act as molecular presses, flattening bowl-shaped corannulene guests. This structural change was confirmed for corannulene and bromocorannulene using X-ray analysis.

Keywords:
cage compoundscorannuleneshost-guest systemssupramolecular chemistryπ interactions

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Area of Science:

  • Supramolecular Chemistry
  • Crystal Engineering
  • Materials Science

Background:

  • Self-assembled coordination cages are advanced supramolecular structures with tunable cavities.
  • Corannulene, a bowl-shaped polycyclic aromatic hydrocarbon, exhibits unique structural properties.
  • Controlling guest molecule conformation within host cavities is a key challenge in supramolecular chemistry.

Purpose of the Study:

  • To investigate the conformational changes of corannulene guests within self-assembled coordination cages.
  • To demonstrate the 'molecular press' effect using corannulene as a model guest.
  • To characterize the host-guest interactions and the resulting guest structure.

Main Methods:

  • Synthesis of box-like self-assembled coordination cages.
  • Inclusion complex formation with corannulene and bromocorannulene.
  • Single-crystal X-ray diffraction analysis to determine molecular structures.

Main Results:

  • Coordination cages effectively act as molecular presses, significantly flattening the bowl-shaped corannulene guest.
  • Pairwise inclusion of corannulene with naphthalene diimide and dimer inclusion of bromocorannulene were observed.
  • X-ray crystallography unambiguously confirmed the compressed structures of corannulene within the cages.

Conclusions:

  • Self-assembled coordination cages can induce significant structural deformation in guest molecules.
  • The 'molecular press' concept is validated for corannulene guests, showcasing host-induced flattening.
  • Precise structural characterization via X-ray analysis confirms the efficacy of these supramolecular hosts.