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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

14.2K
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...
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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...
3.3K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

13.4K
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...
13.4K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

16.9K
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.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
16.9K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

10.8K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
10.8K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.3K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
3.3K

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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A Highly Strained All-Phenylene Conjoined Bismacrocycle.

Xinyu Zhang1, Hong Shi2, Guilin Zhuang3

  • 1Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering,iChEM, University of Science and Technology of China, Hefei, Anhui Province, 230026, China.

Angewandte Chemie (International Ed. in English)
|May 4, 2021
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel, highly strained bismacrocycle, conjoined (1,4)[10]cycloparaphenylenophane (SCPP[10]). This unique structure forms the first peanut-shaped host-guest complex with a fullerene derivative.

Keywords:
conjoined bismacrocyclesstrained moleculessupramolecular interactionstwisted benzene

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Cycloparaphenylenophanes are macrocyclic hydrocarbons with unique structural and electronic properties.
  • Highly strained macrocycles offer opportunities for novel chemical reactivity and host-guest complexation.
  • Developing precise synthetic methods for complex molecular architectures is crucial in chemistry.

Purpose of the Study:

  • To report the precise synthesis of a novel 3D highly strained all-phenylene bismacrocycle.
  • To characterize the structure and strain energy of the synthesized bismacrocycle.
  • To investigate the host-guest complexation behavior of the bismacrocycle with a fullerene derivative.

Main Methods:

  • Precise organic synthesis techniques were employed for macrocycle construction.
  • Scanning tunneling microscopy (STM) was used for real-space atomic-scale structural confirmation.
  • Theoretical calculations were performed to determine strain energy and conformational properties.

Main Results:

  • A 3D highly strained all-phenylene bismacrocycle, conjoined (1,4)[10]cycloparaphenylenophane (SCPP[10]), was successfully synthesized.
  • STM confirmed the conjoined structure at the atomic scale.
  • Theoretical calculations revealed a high strain energy (110.59 kcal mol⁻¹) and a large interphenylene torsion angle (46.07°).
  • A 1:2 host-guest complex of SCPP[10] with [6,6]-phenyl-C61-butyric acid methyl ester was formed, exhibiting a peanut shape.

Conclusions:

  • The precise synthesis of the highly strained SCPP[10] bismacrocycle was achieved.
  • The unique structure and high strain energy of SCPP[10] were experimentally and theoretically validated.
  • SCPP[10] serves as a novel host for fullerene derivatives, forming the first peanut-shaped 1:2 host-guest complex based on bismacrocycles.