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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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Newman Projections02:06

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Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as...
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Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

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Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

2.8K
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.
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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...
2.9K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

14.9K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Spatial Separation of Molecular Conformers and Clusters
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A Germapyramidane Switches Between 3D Cluster and 2D Cyclic Structures in Single-Electron Steps.

Peter Coburger1, Fabio Masero1, Jonas Bösken1

  • 1Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1-5/10, 8093, Zürich, Switzerland.

Angewandte Chemie (International Ed. in English)
|September 24, 2022
PubMed
Summary

A novel germanium cluster, [Ge(η⁴-IDP)]²⁺, transforms between 3D and 2D aromatic structures via reversible redox reactions. This discovery offers insights into inorganic cluster chemistry and aromaticity transformations.

Keywords:
AromaticityCluster CompoundsDensity Functional CalculationsMain-Group ElementsRedox Chemistry

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Area of Science:

  • Organometallic Chemistry
  • Inorganic Cluster Chemistry
  • Aromaticity Studies

Background:

  • Exploration of heavy analogues to known carbon clusters is crucial for understanding periodic trends in bonding and structure.
  • The synthesis and characterization of novel polycyclic compounds with unique electronic properties remain a significant challenge in inorganic chemistry.
  • Understanding redox-driven structural transformations is key to designing new functional materials.

Purpose of the Study:

  • To synthesize and characterize a novel dicationic germanium cluster incorporating an imidazolium-substituted diphosphide ligand.
  • To investigate the redox behavior of the synthesized germanium cluster and its subsequent structural rearrangements.
  • To elucidate the mechanism of the 3D cluster to 2D aromatic ring transformation using computational and experimental methods.

Main Methods:

  • Synthesis of the dicationic germanium cluster [Ge(η⁴-IDP)]²⁺ using GeCl₂⋅dioxane and KBArF₂₄.
  • Electrochemical studies including cyclic voltammetry to probe reversible one-electron reductions.
  • Density Functional Theory (DFT) calculations and solution NMR spectroscopy to elucidate reaction mechanisms and structural characterization.

Main Results:

  • Successful synthesis of the spherical-aromatic nido-cluster [Ge(η⁴-IDP)]²⁺, a heavy analogue of pyramidane.
  • Observation of two reversible one-electron reductions leading to a radical cation and a neutral Ge(II) species.
  • Demonstration of redox-isomerization: reduction induces a transformation from a 3D cluster to a planar 2D aromatic digermolide, reversible upon oxidation.

Conclusions:

  • The synthesized germanium cluster exhibits unique redox-isomerization behavior, transitioning between 3D and 2D aromaticity.
  • These findings provide a rare example of a fundamental transformation between cluster and ring aromatic compounds driven by redox processes.
  • The study highlights the potential of germanium clusters in exploring novel bonding paradigms and dynamic structural chemistry.