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Conformations of Cyclohexane

Conformations of Cyclohexane

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...

Stability of Conjugated Dienes

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

Chair Conformation of Cyclohexane

Chair Conformation of Cyclohexane

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...

Stability of Substituted Cyclohexanes

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...

Conformations of Cycloalkanes

Conformations of Cycloalkanes

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...

SN2 Reaction: Transition State

S_N2 Reaction: Transition State

An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
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Updated: Nov 2, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Flat corannulene: when a transition state becomes a stable molecule.

Ephrath Solel¹, Doron Pappo², Ofer Reany³

¹The Schulich Faculty of Chemistry, Technion - Israel Institute of Technology Technion City Haifa 3200001 Israel keinan@technion.ac.il ephrath.solel@gmail.com.

Chemical Science

|June 7, 2021

Summary

This summary is machine-generated.

Researchers synthesized a planar corannulene derivative, decakis(t-butylsulfido)corannulene, challenging its prior classification as merely a transition state. This discovery opens new avenues for exploring unique molecular geometries in organic chemistry.

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Area of Science:

Organic Chemistry
Computational Chemistry
Materials Science

Background:

Corannulene typically exists in a bowl-shaped conformation, with planar geometry considered a transient state.
Steric repulsion from substituents is hypothesized to stabilize a planar corannulene structure.

Purpose of the Study:

To investigate the effect of bulky substituents on corannulene's conformational stability.
To determine if a planar corannulene derivative can be isolated.

Main Methods:

Computational modeling using M06-2X/def2-TZVP and B3LYP/def2-TZVP methods.
Synthesis of decakis(t-butylsulfido)corannulene from decachlorocorannulene.
X-ray crystallographic analysis of the synthesized compound.

Main Results:

Theoretical calculations predicted two low-energy structures: a planar and a bowl-shaped conformation for decakis(t-butylsulfido)corannulene.
The compound was successfully synthesized under mild conditions.
X-ray crystallography confirmed the existence of two polymorphs: one with a flat corannulene core and another with a bowl-shaped core.

Conclusions:

The steric bulk of t-butylsulfido groups effectively stabilizes a planar corannulene framework.
Decakis(t-butylsulfido)corannulene represents the first isolable example of a planar corannulene derivative.
The study validates computational predictions and demonstrates synthetic accessibility of unusual molecular geometries.