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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

13.0K
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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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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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...
12.1K
Three-Dimensional Analysis of Strain01:29

Three-Dimensional Analysis of Strain

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Three-dimensional strain analysis is crucial for understanding how materials deform under stress, particularly in elastic, homogeneous materials. This method employs principal stress axes to simplify complex stress states into more understandable forms. Subjected to stress, a small cubic element within a material either expands or contracts along these axes, transforming into a rectangular parallelepiped. This transformation effectively illustrates the material's deformation. The principal...
289
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

15.1K
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...
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Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.1K
Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the...
1.1K
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

48.9K
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Synthesis of a highly strained deep cavitand.

M Saeed Mirzaei1, Saber Mirzaei1,2, Hormoz Khosravi1

  • 1Department of Chemistry, Rice University, 6100 Main St., Houston, TX 77005, USA. raulhs@rice.edu.

Chemical Communications (Cambridge, England)
|August 19, 2025
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Summary

Researchers synthesized a stable, highly strained deep cavitand molecule. This molecule features a large cavity suitable for hosting fullerenes, addressing a key challenge in strained molecule synthesis.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Accessing highly strained molecules presents significant synthetic challenges.
  • Developing novel molecular architectures with unique properties is crucial for advancing chemical science.

Purpose of the Study:

  • To report the synthesis of a novel, bench-stable, and highly strained deep cavitand.
  • To characterize the structural features and potential applications of the synthesized cavitand.

Main Methods:

  • A two-step synthetic protocol was employed using known starting materials.
  • Spectroscopic and crystallographic methods were used for characterization (details not provided in abstract).

Main Results:

  • A highly strained deep cavitand (molecule 1) with a strain energy of approximately 135 kcal mol⁻¹ was successfully synthesized.
  • The rigid structure of cavitand 1, composed of four arch-shaped biphenyelenes, creates a large internal cavity (approximately 500 ų).

Conclusions:

  • The developed protocol provides efficient access to a unique, highly strained deep cavitand.
  • The large cavity of cavitand 1 makes it a promising host molecule for fullerenes and potentially other guests.