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Related Concept Videos

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,...
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...
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
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...
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

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...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

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

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Unsymmetrical triangular Schiff base macrocycles with cone conformations.

Jian Jiang1, Mark J Maclachlan

  • 1Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, Canada V6T 1Z1.

Organic Letters
|February 6, 2010
PubMed
Summary
This summary is machine-generated.

Two novel unsymmetrical Schiff base macrocycles were synthesized and characterized. These triangular macrocycles exhibit dynamic conformational changes and effectively bind organic cations.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Physical Chemistry

Background:

  • Schiff base macrocycles are important in host-guest chemistry.
  • Dynamic conformational behavior in macrocycles influences their binding properties.

Purpose of the Study:

  • To synthesize and characterize new unsymmetrical Schiff base macrocycles.
  • To investigate the dynamic conformational interconversion of these macrocycles.
  • To evaluate their potential as hosts for organic cations.

Main Methods:

  • Organic synthesis of unsymmetrical Schiff base macrocycles.
  • Variable-temperature Nuclear Magnetic Resonance (NMR) spectroscopy to study conformational dynamics.
  • Host-guest binding studies with organic cations.

Main Results:

  • Successful synthesis of two new unsymmetrical Schiff base macrocycles with isosceles triangle shapes.
  • Macrocycles adopt cone-shaped conformations that interconvert rapidly at elevated temperatures.
  • Dynamic NMR studies revealed slower flipping dynamics for the keto-enamine tautomer compared to the enol-imine form.
  • Demonstrated effective host-guest complexation of organic cations within the macrocyclic cavities.

Conclusions:

  • The synthesized macrocycles possess unique dynamic properties influenced by tautomerization.
  • These macrocycles show promise as selective hosts for organic cations in supramolecular chemistry applications.