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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.8K
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...
13.8K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

3.8K
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.
3.8K
Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

14.6K
The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene.  The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
14.6K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

16.5K
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...
16.5K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.1K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
3.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.2K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.2K

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Hexaphenylditetrels - When Longer Bonds Provide Higher Stability.

Lars Rummel1, Jan M Schümann1, Peter R Schreiner1

  • 1Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, 35392, Giessen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 4, 2021
PubMed
Summary

Heavier tetrel hexaphenylethane derivatives are stable due to London dispersion interactions. Longer central bonds allow phenyl groups to maximize these stabilizing interactions, unlike the carbon analog.

Keywords:
C−H-π-interactionsLondon dispersionPauli repulsionbond dissociation energybond strength

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Area of Science:

  • Computational chemistry
  • Organic chemistry
  • Quantum chemistry

Background:

  • Hexaphenylethane is known for its instability.
  • Heavier tetrel analogs of hexaphenylethane are surprisingly stable and preparable.

Purpose of the Study:

  • To investigate the origin of thermodynamic stability in heavier tetrel hexaphenylethane derivatives.
  • To compare their stability against dissociation with the parent carbon compound.

Main Methods:

  • Computational analysis using local energy decomposition (LED) and symmetry-adapted perturbation theory (SAPT).
  • High-level theoretical calculations at DLPNO-CCSD(T)/def2-TZVP and sSAPT0/def2-TZVP levels.

Main Results:

  • London dispersion (LD) interactions were identified as the primary factor for stability.
  • Longer central tetrel-tetrel bonds facilitate optimal phenyl group positioning for LD interactions.

Conclusions:

  • The enhanced stability of heavier tetrel hexaphenylethane derivatives is attributed to favorable London dispersion forces.
  • Molecular design leveraging longer bonds can enhance stability through non-covalent interactions.