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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.2K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.8K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.8K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.3K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.3K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.1K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.7K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.7K

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Facilitating Electron Transfer by Resizing Cyclocarbon Acceptor from C18 to C16.

O A Stasyuk1, A A Voityuk1, A J Stasyuk1,2,3,4

  • 1Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, C/ Maria Aurèlia, Capmany 69, 17003, Girona, Catalonia, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 26, 2024
PubMed
Summary

Cyclocarbon molecules like C16 and C18 show strong electron-withdrawing properties. Their complexes facilitate rapid photoinduced electron transfer, with C16 accelerating reactions due to lower reorganization energy.

Keywords:
Charge transferCyclocarbonsExcited statePhotoinduced electron transferReorganization energy

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Area of Science:

  • * Supramolecular chemistry and materials science.
  • * Computational chemistry and theoretical physics.

Background:

  • * Recent synthetic advancements enable the creation of novel cyclocarbon molecules.
  • * On-surface chemistry and tip-induced reactions are key formation methods.
  • * Cyclocarbons are being explored for their unique electronic properties.

Purpose of the Study:

  • * To computationally investigate the electronic properties of C16 and C18 cyclocarbons.
  • * To analyze van der Waals (vdW) complexes of cyclocarbons with donor and acceptor molecules.
  • * To understand the dynamics of photoinduced electron transfer (ET) in these systems.

Main Methods:

  • * Density Functional Theory (DFT) calculations.
  • * Analysis of van der Waals interactions and complex formation.
  • * Calculation of reorganization energies and electron transfer rates.

Main Results:

  • * Cyclocarbon molecules exhibit significant electron-withdrawing capabilities.
  • * vdW complexes show thermodynamically favorable photoinduced electron transfer from donors to cyclocarbons.
  • * Electron transfer occurs on a picosecond timescale.
  • * C16 demonstrates faster ET reactions than C18 due to lower reorganization energy.

Conclusions:

  • * Cyclocarbons are promising candidates for electron acceptor materials.
  • * The electron transfer dynamics are highly dependent on molecular structure and properties.
  • * C16 and C18 show potential for applications in molecular electronics and photocatalysis.