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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...

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...

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

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...

Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

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Published on: August 2, 2012

Aggregation Behavior of Cyclodextrin-Based [3]Rotaxanes.

Yosuke Akae^1,2,3, Patrick Theato^1,4

¹Institute for Chemical Technology and Polymer Chemistry (ITCP), Karlsruhe Institute of Technology (KIT), 76131, Karlsruhe, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|June 5, 2023

Summary

This summary is machine-generated.

Researchers observed and analyzed the hexagonal packing aggregation of cyclodextrin (CD)-based [3]rotaxanes for the first time. This aggregation is driven by hydrogen bonds between CD units, unlike polymer structures.

Keywords:

cyclodextrins hydrogen bonding rotaxanes self-assembly solvent effects

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Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

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Published on: June 20, 2019

Area of Science:

Supramolecular Chemistry
Materials Science

Background:

Cyclodextrin (CD)-based polyrotaxanes are known to exhibit hexagonal packing aggregation.
Studies on the aggregation behavior of non-polymeric rotaxanes are scarce due to molecular design challenges.

Purpose of the Study:

To investigate and analyze the aggregation behavior of cyclodextrin (CD)-based [3]rotaxanes.
To determine the driving forces behind the aggregation of these non-polymeric rotaxane systems.

Main Methods:

Synthesis of [3]rotaxane species using a urea-end-capping method.
Evaluation of aggregation behavior using X-ray Diffraction (XRD) and Scanning Electron Microscopy (SEM).

Main Results:

[3]Rotaxane species with native cyclodextrin rings demonstrated hexagonal packing aggregation, confirmed by XRD.
Per-acetylated cyclodextrin derivatives did not exhibit this aggregation behavior.
Hydrogen bonding among cyclodextrin units was identified as the primary driving force for aggregation.

Conclusions:

Cyclodextrin-based [3]rotaxanes are capable of hexagonal packing aggregation.
Hydrogen bonding is crucial for the aggregation of these supramolecular structures.
The study provides insights into the molecular design and aggregation mechanisms of non-polymeric rotaxanes.