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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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 staggered...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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 tetrahedral value,...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...

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Related Experiment Video

Updated: Jun 30, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

An interdigitated functionally rigid [2]rotaxane.

Il Yoon1, Ognjen S Miljanić, Diego Benítez

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.

Chemical Communications (Cambridge, England)
|September 26, 2008
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel donor-acceptor [2]rotaxane featuring naphthalene rings and a cyclophane. In solid form, these molecules form interdigitated pi-pi stacks, creating a unique superstructure.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in molecular machines.
  • Donor-acceptor systems are crucial for charge-transfer processes and advanced materials.

Purpose of the Study:

  • To synthesize and characterize a functionally rigid [2]rotaxane incorporating pi-electron rich naphthalene units and a pi-electron deficient tetracationic cyclophane.
  • To investigate the solid-state self-assembly and supramolecular architecture of this novel donor-acceptor rotaxane.

Main Methods:

  • Template-directed synthesis utilizing a tetracationic cyclophane as a template.
  • Solid-state structural analysis using X-ray crystallography.

Main Results:

  • Successful synthesis of a [2]rotaxane featuring 1,5-disubstituted naphthalene (NP) ring systems threaded by cyclobis(paraquat-p-phenylene).
  • In the solid state, the donor-acceptor rotaxane molecules self-assemble into parallel pi-pi stacks.
  • These stacks exhibit an interdigitated superstructure with alternating NP ring systems and bipyridinium units.

Conclusions:

  • The described rotaxane represents a new class of donor-acceptor supramolecular architectures.
  • The observed pi-pi stacking in the solid state highlights the potential for ordered assembly in rotaxane-based materials.
  • This work provides a foundation for designing functional materials with controlled solid-state organization.