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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.3K
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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Catenins01:23

Catenins

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Catenins are characterized by multiple binding domains and dynamic structures that allow them to function as linker proteins in cell junction complexes. All catenins, except α-catenin, contain a characteristic protein sequence called the armadillo repeat and are therefore also called armadillo proteins.
Catenins in Cell Junctions
Catenins bind to cell adhesion molecules such as cadherins and link them to different cytoskeletal proteins depending on the type of cell junction. At the...
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.3K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
4.3K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

17.3K
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...
17.3K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

21.4K
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...
21.4K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

16.7K
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...
16.7K

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How Small Can a Catenane Be?

Xuejun Feng1, Jiande Gu2, Qun Chen1

  • 1School of Petrochemical Engineering, Changzhou University , Changzhou 213164, China.

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|November 19, 2015
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Summary
This summary is machine-generated.

Researchers explored the smallest viable catenane, finding [C15H30]2 may be the minimum size to resist fragmentation. Computational methods analyzed the stability of interlocked cycloalkanes.

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Area of Science:

  • Supramolecular Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Catenanes are mechanically interlocked molecules with growing importance in supramolecular chemistry.
  • Understanding the structural and energetic limits of catenanes is crucial for their application.

Purpose of the Study:

  • To determine the minimum number of carbon atoms required for a stable [2]catenane structure.
  • To investigate the energetic stability and structural properties of saturated n-cycloalkane catenanes ([CnH2n]2).

Main Methods:

  • Employed density functional theory (B3LYP, BP86, M06-2X) and molecular mechanics (MM3, MM4) methods.
  • Studied representative [2]catenane models composed of two interlocked saturated n-cycloalkanes.
  • Analyzed structural parameters, energy variations, and electron density differences.

Main Results:

  • Structural and energetic properties varied nearly monotonically from n=18 to n=11.
  • Dissociation energies increased with decreasing ring size (e.g., B3LYP/DZP++: 101 kcal/mol for n=18 to 323 kcal/mol for n=11).
  • Longest C-C bond distances showed a trend with a notable "shoulder" around n=14, suggesting [C15H30]2 as a potential minimum size.

Conclusions:

  • The study provides insights into the stability of small catenanes.
  • [C15H30]2 is identified as the smallest catenane likely to resist fragmentation under specific laboratory conditions.
  • Computational methods reveal trends in catenane stability related to ring size.