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Related Concept Videos

Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

15.7K
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...
15.7K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

20.2K
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...
20.2K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.6K
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...
16.6K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.1K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
4.1K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

4.0K
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.
4.0K
Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

18.5K
In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...
18.5K

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Conformational behavior and stacking interactions of contorted polycyclic aromatics.

Yanfei Guan1, Matthew L Jones, Alyssa E Miller

  • 1Department of Chemistry, Texas A&M University, College Station, TX 77843, USA.

Physical Chemistry Chemical Physics : PCCP
|May 18, 2017
PubMed
Summary
This summary is machine-generated.

Computational analysis reveals that molecular curvature in contorted polycyclic aromatic compounds influences stacking interactions. Modifications like thiophene rings and B/N atoms can enhance dimer formation, but curvature doesn't always guarantee stronger stacking.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Contorted polycyclic aromatic compounds (CPACs) exhibit unique 3D structures.
  • Their saddle-shape and concave surfaces influence intermolecular interactions.
  • Understanding these interactions is key for designing materials with specific solid-state packing.

Purpose of the Study:

  • To systematically analyze the conformations and stacking interactions of 18 CPACs.
  • To investigate how molecular curvature affects stacking strength.
  • To guide the design of CPACs with tunable solid-state properties.

Main Methods:

  • Systematic computational analysis using B97-D3M(BJ)/TZV(2d,2p)//B97-D/TZV(2d,2p) level of theory.
  • Evaluation of low-lying conformations and stacking affinities.
  • Analysis of intermolecular non-covalent interactions.

Main Results:

  • Significant variations observed in conformations and stacking affinities among the studied CPACs.
  • Introduction of peripheral thiophene rings and B/N atoms in the core enhances stacked dimer formation.
  • Curvature alone does not consistently lead to stronger stacking interactions.

Conclusions:

  • Molecular design, including peripheral and core modifications, is crucial for controlling CPAC stacking.
  • The study provides insights into structure-property relationships for CPACs.
  • Findings aid in the rational design of CPACs for targeted solid-state applications.