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Conformations of Cyclohexane

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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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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...

Chair Conformation of Cyclohexane

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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.
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Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
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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...

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Twisted Nanographenes with Robust Conformational Stability.

Penghui Song¹, Yoshifumi Hashikawa², Chaolumen¹

¹College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China.

Nanomaterials (Basel, Switzerland)

|November 8, 2024

Summary

This summary is machine-generated.

This study reveals the remarkable conformational stability of a novel double-twisted nanographene. Its unique structure, featuring four [6]helicene units, resists racemization until temperatures surpass 200 °C.

Keywords:

helicene nanographene twist

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Area of Science:

Organic Chemistry
Materials Science
Supramolecular Chemistry

Background:

Selective synthesis of twisted nanographenes remains challenging, often yielding mixtures of geometries.
High activation barriers typically prevent interconversion between different nanographene structures.
Previously, a double-twisted nanographene with four [6]helicene units was synthesized.

Purpose of the Study:

To investigate the conformational stability of the synthesized double-twisted nanographene.
To determine the racemization temperature and the rate-determining step for conformational changes.
To provide experimental and computational insights into the structural robustness of complex nanographenes.

Main Methods:

Experimental analysis of conformational changes at varying temperatures.
Computational modeling to simulate molecular dynamics and energy barriers.
Racemization studies to identify the critical step in structural rearrangement.

Main Results:

The double-twisted nanographene exhibits robust conformational stability.
Racemization occurs only at temperatures exceeding 200 °C.
The initial flip of a single [6]helicene unit was identified as the rate-determining step for racemization.

Conclusions:

The synthesized nanographene possesses exceptional thermal stability due to its unique twisted architecture.
The study elucidates the mechanism of conformational change in complex helical nanostructures.
Findings contribute to the rational design of stable, geometrically defined nanographenes for advanced applications.