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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...

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.

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...

Radical Reactivity: Steric Effects

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...

Resonance and Hybrid Structures

Resonance and Hybrid Structures

According to the theory of resonance, if two or more Lewis structures with the same arrangement of atoms can be written for a molecule, ion, or radical, the actual distribution of electrons is an average of that shown by the various Lewis structures.
Resonance Structures and Resonance Hybrids
The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N–O and N=O bonds.

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...

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Related Experiment Video

Updated: Mar 22, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Unusually Stable Triazine-based Organic Superstructures.

Sun-Min Jung¹, Dongwook Kim², Dongbin Shin³

¹School of Energy and Chemical Engineering, Center for Dimension Controllable Organic Frameworks, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST, Ulsan, 44919, Korea.

Angewandte Chemie (International Ed. in English)

|April 28, 2016

Summary

This summary is machine-generated.

Researchers created novel superstructures using solid-state reactions of organic single crystals. This efficient method yields materials with unique channels, high thermal stability, and electron-beam tolerance.

Keywords:

interdigitation porous organic crystals single-crystals solid-state reactions superstructures

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Published on: February 15, 2016

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Area of Science:

Organic Chemistry
Materials Science
Crystallography

Background:

Solid-state reactions offer advantages over liquid-phase methods in organic synthesis.
The formation of complex superstructures from simple organic precursors is an area of active research.

Purpose of the Study:

To demonstrate the formation of a novel superstructure via a solid-state reaction of an organic single crystal.
To characterize the structural and property attributes of the resulting superstructure.

Main Methods:

Cyclotrimerization of 1,3,5-tricyanobenzene (TCB) single crystals.
Single crystal X-ray diffraction for structural confirmation.
Transmission electron microscopy for visualization.

Main Results:

Formation of a 5,5',5''-(1,3,5-triazine-2,4,6-triyl)triisophthalonitrile (TIPN) superstructure.
The superstructure exhibits hexagonally packed 1-dimensional (1D) channels.
Interdigitated nitrile interactions stabilize the crystal lattice.

Conclusions:

Solid-state cyclotrimerization is an effective route to TIPN superstructures.
The resulting superstructures possess high thermal stability and electron-beam tolerance.
The unique channel structure holds potential for advanced material applications.