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Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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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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In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
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Ionic Radii

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Ionic radius is the measure used to describe the size of an ion. A cation always has fewer electrons and the same number of protons as the parent atom; it is smaller than the atom from which it is derived. For example, the covalent radius of an aluminum atom (1s22s22p63s23p1) is 118 pm, whereas the ionic radius of an Al3+ (1s22s22p6) is 68 pm. As electrons are removed from the outer valence shell, the remaining core electrons occupying smaller shells experience a greater effective nuclear...
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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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Contractile rings are composed of microfilaments and are responsible for separating the daughter cells during cytokinesis. Contractile ring assembly proceeds along with other cell cycle events; however, very few mechanistic details are known about the timing and coordination of the contractile rings with the cell cycle.
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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
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Endocircular Li Carbon Rings.

Yi-Fan Yang1, Lorenz S Cederbaum1

  • 1Theoretical Chemistry, Institute of Physical Chemistry, Universität Heidelberg, Im Neuenheimer Feld 229, Heidelberg, Germany.

Angewandte Chemie (International Ed. in English)
|May 18, 2021
PubMed
Summary
This summary is machine-generated.

Monocyclic carbon rings can host lithium (Li) atoms, forming unique charge-separated and neutral states. In larger rings like Li@C24, neutral states become dominant, suggesting van-der-Waals interactions.

Keywords:
ab initio calculationsdonor-acceptor systemselectron transferguest atomsmonocyclic carbon rings

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Area of Science:

  • Computational chemistry
  • Materials science
  • Quantum mechanics

Background:

  • Investigating the electronic properties of endohedral fullerenes and carbon nanostructures.
  • Understanding the interactions between guest atoms and carbon cages.

Purpose of the Study:

  • To determine if monocyclic carbon rings can encapsulate lithium (Li) atoms.
  • To analyze the electronic states and binding characteristics of Li within carbon rings.

Main Methods:

  • Utilizing accurate many-electron quantum-chemistry methods.
  • Analyzing low-lying electronic states, including charge-separated and neutral configurations.
  • Calculating electron binding energies and binding strengths.

Main Results:

  • Confirmed that monocyclic carbon rings can accommodate Li atoms.
  • Identified both charge-separated (Li+ and ring-) and neutral (Li and ring) electronic states.
  • Observed a drastic increase in electron binding energies with ring size, with the neutral state becoming ground state in Li@C24.
  • Indicated weak, van-der-Waals type binding for Li in neutral states.

Conclusions:

  • Monocyclic carbon rings exhibit versatile electronic behavior when encapsulating Li.
  • The electronic properties are strongly dependent on ring size and geometry.
  • Potential for novel materials with tunable electronic properties.