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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

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...
Chair Conformation of Cyclohexane02:02

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 staggered...
Conformations of Cyclohexane02:11

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 tetrahedral value,...
Conformations of Cycloalkanes02:29

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 was based on the...
Stability of Conjugated Dienes01:28

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.
UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...

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Probing C84-embedded Si Substrate Using Scanning Probe Microscopy and Molecular Dynamics
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Search for suitable approximation methods for fullerene structure and relative stability studies: case study with

Wei Quan Tian1, Ji-Kang Feng, Yan Alexander Wang

  • 1Department of Material Sciences, Faculty of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga, Fukuoka 816-8580, Japan. wqtian@cube.kyushu-u.ac.jp

The Journal of Chemical Physics
|September 13, 2006
PubMed
Summary

Density functional theory methods accurately predict fullerene structures. HCTH with the 3-21G basis set excels in predicting C60 and C70 geometries and C50 isomer stability.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Quantum Mechanics

Background:

  • Fullerenes (C60 and C70) are crucial in materials science.
  • Accurate structural prediction is vital for understanding fullerene properties.
  • Various density functional theory (DFT) methods exist, each with unique strengths.

Purpose of the Study:

  • To evaluate the performance of different DFT methods for fullerene geometry prediction.
  • To identify the most effective DFT methods for predicting the relative stability of C50 isomers.
  • To compare the electronic properties, specifically the HOMO-LUMO gap, predicted by various DFT functionals.

Main Methods:

  • Geometry optimization of C60 and C70 using LDA, GGA, and hybrid DFT methods.
  • Application of the HCTH functional with the 3-21G basis set.
  • Utilizing the PM3 semi-empirical method for initial screening of C50 isomers.
  • Analysis of the highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) gap.

Main Results:

  • The HCTH method with the 3-21G basis set demonstrated excellent performance in predicting fullerene structures.
  • PM3 proved efficient for preliminary identification of stable C50 isomers.
  • HCTH/3-21G provided C50 geometries comparable to B3LYP/6-31G(d).
  • A clear descending order of predicted HOMO-LUMO gaps was established across different DFT functional types.

Conclusions:

  • HCTH/3-21G is a highly recommended method for fullerene structural predictions.
  • DFT methods offer valuable insights into fullerene stability and electronic properties.
  • The choice of DFT functional significantly impacts the prediction of electronic band gaps.