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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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Thermal Electrocyclic Reactions: Stereochemistry01:17

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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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.
2.9K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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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.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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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
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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A [3]Rotaxane Containing {Ti7Ga} Rings Linking CuII: Synthesis, Structure, and Spectroscopic Studies.

Selena J Lockyer1, Lubomir Loci1, George F S Whitehead1

  • 1Department of Chemistry and Photon Science Institute, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 30, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized extended hybrid organic-inorganic rotaxanes using novel building blocks. These structures, featuring copper complexes, form extended [3]rotaxanes and [2]rotaxanes, with their assembly controlled by steric factors and confirmed by spectroscopy.

Keywords:
DEER/PELDOREPRheterometallic ringsrotaxanessupramolecular

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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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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Coordination Chemistry

Background:

  • Development of complex molecular architectures like rotaxanes is crucial for advanced materials.
  • Hybrid organic-inorganic materials offer unique properties by combining different chemical entities.
  • Controlling the self-assembly of molecular components is a key challenge in supramolecular chemistry.

Purpose of the Study:

  • To synthesize and characterize extended hybrid organic-inorganic rotaxanes.
  • To investigate the influence of thread structure on rotaxane formation and architecture.
  • To explore the structural integrity and dynamics of these rotaxanes in solution.

Main Methods:

  • Synthesis of anionic macrocycle and pyridyl-terminated secondary ammonium thread building blocks.
  • Reaction with copper(II) bis(hexafluoroacetylacetonate) ([Cu(hfac)2]) to form rotaxane complexes.
  • Characterization using single-crystal X-ray crystallography and Double Electron-Electron Resonance (DEER) spectroscopy.

Main Results:

  • Successful synthesis of extended [3]rotaxane ({[Cu(hfac)2]3[1]2}) and [2]rotaxane ({[Cu(hfac)2]2[3]}).
  • Steric demands of the organic thread's arms dictate the final rotaxane structure.
  • A linear Cu…Cu…Cu fragment with a 31.3 Å separation was observed in the [3]rotaxane.
  • DEER spectroscopy confirmed the structural integrity in solution and revealed dynamic rearrangements.

Conclusions:

  • Extended hybrid organic-inorganic rotaxanes can be controllably synthesized.
  • The molecular design of the organic thread is critical for directing self-assembly.
  • These rotaxanes exhibit stable structures in solution, with evidence of dynamic behavior.