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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.2K
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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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.7K
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,...
9.7K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

13.7K
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...
13.7K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

12.9K
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...
12.9K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

16.1K
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...
16.1K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

12.8K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
12.8K

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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
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Trioxazolo[23]metacyclophane: synthesis, structural analysis, and optical properties.

Hao Yu1, Danielle L Gray2, Toby J Woods2

  • 1Department of Chemical and Biomolecular Engineering, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave., Urbana, IL 61801, USA.

Acta Crystallographica. Section C, Structural Chemistry
|February 4, 2022
PubMed
Summary

Researchers synthesized a novel conjugated macrocycle, trioxazolo[2^3]metacyclophane, using the van Leusen reaction. Its unique twisted saddle shape and electronic properties were characterized, revealing potential for advanced material applications.

Keywords:
conjugated macrocyclecrystal structuregel permeation chromatographymetacyclophanevan Leusen MCRsvan Leusen reaction

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Conjugated macrocycles are crucial in supramolecular chemistry and materials science.
  • The van Leusen reaction offers a versatile route to heterocyclic compounds.

Purpose of the Study:

  • To synthesize and characterize a novel conjugated macrocycle, trioxazolo[2^3]metacyclophane (M).
  • To investigate the molecular structure and electronic properties of M.

Main Methods:

  • Multicomponent van Leusen reaction for synthesis.
  • Nuclear Magnetic Resonance (NMR) spectroscopy, mass spectrometry, and gel permeation chromatography (GPC) for characterization.
  • Single-crystal X-ray crystallography, X-ray diffraction (XRD), absorption and emission spectroscopy, and density functional theory (DFT) calculations for structural and electronic analysis.

Main Results:

  • Successful synthesis of trioxazolo[2^3]metacyclophane (M).
  • M exhibits a twisted saddle-like molecular structure.
  • Analysis revealed significant π-π interactions between molecules.
  • Electronic properties were studied using spectroscopy and DFT.

Conclusions:

  • The study reports the successful synthesis and comprehensive characterization of a novel conjugated macrocycle.
  • The unique structure and electronic properties of M suggest potential applications in advanced materials.